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Please login or sign up for a free trial to access the full content.2.2.3.1 Hydroboration of Ketones Catalyzed by Oxazaborolidines
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Zaidlewicz, M.; Pakulski, M. M., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 96.
The reduction of ketones with borane/oxazaborolidines, discovered by Itsuno[208,209] and developed by Corey,[210,211] is a widely used method for the asymmetric synthesis of secondary alcohols. Several reviews are available.[212–223]
Meeeeeeeeeeeeeee 88 eee ee eeeeeeeee eeee B-eeeee eeeeeeee ee eeeeeeee eeee eeeeee, eeeeeee eeeee, eeeeeeee, ee eeeeeee (Meeeee 88). Mee M—M eeee ee eeeeeeeeeeeee eeeeeeeeeeeeeeee 88 (M8 = M) ee eee eeeeeeee eeeeee eeeeeee. Meeeeee, eeeeeee eeeeeee eeeeeeeeee ee eee Meeee eeeee eeeeeeee eeee.
Meeeee 88 Meeeeeeeee ee Meeeeeeeeeeeeeee eee Meeeeeeeeeee ee Meeeeee
Meeeeeee eeeeee eeeeeeeeee ee eee Meeee eeeeee eeeee eeee. Meeeeeeeeeee, eeee eeeeeeeeee eee eeeeeeeee eee eeeeeee ee eeeeeeeee, eeeeeeeee ee eeee eeeeee eeeeeeeee eeee ee eee eeeeeee ee eee eeeeeeeeeeeeeee. Meeeeeee, eee eeeeeeeeee ee eeeeeeeeee ee eeeeeeeee eee eeeeeeeeeee eeeeeeee eeeeee eeeee eeeeeeee e eeeeeeeee eeeeeeee, eeeee ee eee Meeee–Meeeee–Meeeeee (MMM) eeeeeeeee. Mee eeeeee ee eeeeeeee eeeeee eeeeeeeee ee eee eeeeeee, eee ee eeeeeee 8–88 eee%. Meeeee eeeeeeeeeeeeeeee eeeeee eeeeeeeeeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeee, eee eee eeeeeeeee ee eeeee ee Meeeee 88.
Meeeee 88 Meeeeeee Meeeeeeee ee eee Meeeeeeee Meeeee Meeeeeeee eeee Meeeee/Meeeeeeeeeeeeeee[888,888]
M-Meeeeeeeeeeeeee 88, eeeeeeeee eeee (M)-8,8-eeeeeeeeeeeeeeee, eeeee eee eeeeeee 88 eeee eeeeee. Meeeee 88 eeeeeeeeee eee eeeeeee ee eee eeeeeeeeee eeeee 88, eeeeeeee eeeeee eeeeeeeeeeee eeee eee eeeeee eeeeee eeeee (MM). Mee eeeeeee eee ee eeeeeeeeeee, eee eeeeeeeeeeee 88 eeeeeeeeee (M)-eeeeeeeeeeeeeeee 88, eee eee eeeeeeee 88 ee eeeeeeeeeee.[888]
M eeeeee/eeeeee eeeee ee 8:8 ee eeeeeeeeee eee eeeeeeeee, eeeeeeeeee eeee eee M—M eeeee eee eeeeeeee ee eee eeeeeeee.[888] Mee eeeeeeeeeeeeeeee 88 eeeeeeeee eeeeeeeeeeeeeeeeee eeee eeee, eeeeeeeee eeeeee eee eeeeeeeeeeeeee 88, eee eeeeeeee ee eee eeeeeeeee,[888] eeeee ee eeeeeeeeeee eeee eee eeeeeee eeeeeee. Me eee eeeeeeeeeeee eee eeeeee/eeeeee eeeee ee eeeee, eee eeeeeeeeeeeeeeee 88 eee eeeee eeee eeeeeeee.
Meeeeeeeeee eeeeeee ee eee eeeeeeeee eee eeeeeeeeeeeeeeeee eeee eeee eeeeeee eee ee ee eeeeee eee eeeeeeeeeeeee eeeeeee.[888–888] Mee eeeeeeeee–eeeeeeee MMMM eeeee eee eeee eeee eeee ee eeeeeee eee eeeeeeeeeeee eeeeee ee eee eeeeeeee eeeeeee.[888] M eeeeee ee eeeeee eeeeeeeeeeeeeeee eeee eeee eeeeeeee eeee eeeeeee B-eeeee eeeeeeee,[888–888] eee eee eeeeeeeeee eee eeeeeeeeee eeeee. Mee eeee eeeeee eeee, eeeeee eeeeeeeee MMM eeeeeeee 88 (Meeeee 88),[888–888,888] eee eeeee ee (M)-8,8-eeeeeeeeeeeeeeee. Meeeeeeeeeeeeeee 88 eee 88[888,888,888] eee eeeeeee-eeeee eeeeeeeee,[888–888] e.e. 88,[888] eee eeee eeeeeeeee eeeeeeeee, eee 88 (M8 = M) eee eeee eeee ee e eeeee-eeeee eeeeeeeee ee (M,M)-eeeeeeeeee, e eeeeee B8-eeeeeeeeee eeeeeeee eeeeeee.[888,888] Meee eeeeeeeeeee ee eee eeeeeee eee ee eeeeeeee eeee eeeeeeeeeeee eeeeeeeee eeeeeeeeeeee eee-8-eeeeeeeeee-8-eee.
Meeeee 88 Meeeeeeeeeeeee Meeeee Meeeeeeeeeeeeeee
Mee (M)- eee (M)-eeeeeee ee 8,8-eeeeeeeeeeeeeeee (88) eee ee eeeeeeee eeee eeeeeeee eeeeeeeee (M)- eee (M)-eeeeeee,[888–888] ee eee (M)-eeeeeeeeee ee eeeeeeeeee ee M-(eeee-eeeeeeeeeeeeee)eeeeeeeeeee ee eee eeeeeeee ee (−)-eeeeeeeee, eeeeeeee ee eeeeeeee eeee eeeeeeeeeeee.[888] Mee eeee eeeeee (M)-eeeeeeeeee eee eeee ee eeeeeeee eeee eeeeeee eeeeeeeeeeee eeee eeeeeeee ee eeeeeeeeee.[888] (M)-8,8-Meeeeeeeeeeeeee ee eeeeeeee ee eee eeeeeeee ee (M)-eeeeee eeeeee eeeee eeeeeeeeeeeee eeee eeeeeeeeeeeeeee eeeeeee.[888,888]
Meeeee eeeeeee 88 (M8 = M), eeeeeeeeeeee eeeeeeeee eee eeee ee eeee, eeeeeeee eeee eeeeeeeeeee ee eee eeeeeeeee ee eeeeeee. Meeeeee, eeee ee eeee eeeeee eeeeeeeee, eeeee eeee eeeee eeeeeeeeeeeeeeee, eee eeeeeeee eee ee eee eeeeee eeee eeeeeeeeeeee eeeeeee.[888–888] Me eeeeeeee, eeeeeeeeeeeeeee 88 (M8 = Me), eeeeeeee eeee eeeeeeeee (M)-8,8-eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeee, ee e eeee-eeeeeee, eeeeeeeeeeee eeeeeeeee eeeee. Mee eeeeeeeee ee eeeeeeeee ee eeeeee,[888] eee e eeeeeeee eeeeeeeee eee eeee eeeeeeee.[888] B-Meeee- eee B-eeee-eeeeeeeeeee eeeeeeeeeeeeeeee eee eeeeeee eeeeeeee eeee eeeee- eee eeeeeeeeeee eeeee eee B-eeeee eeeeeeee ee eeeeeeeee eeeeeee ee e Meee–Meeee eeeeeeeee eeeeeeeeee eeee-eeeeeeeee (888 °M) 8-Å eeeeeeeee eeeeee. Meee eeeeeeeee ee eeeeeee eeeeeeeeee eee eeeeeeeeeeee eeeeeee ee eee eeeeeeeee eeee eeeeee, eeeeeeee eee eeeeeee eee eeeee eeeeeee e eeeee eeeeeeee eeeeeeee (Meeeee 88).
Meeeee 88 Meeeeeeee ee ee Meeeeeeeeeeeeee eeee (M)-8,8-Meeeeeeeeeeeeeee eee Meeeeeeeeeee Meee[888]
Mee eeeeeeee ee eeeeeee 88 eee eeeee e eeeeeeee eeeeee ee eee eeeeeeeeeee, ee eeeeeeee ee eee eeeeeeeee ee eeeeeeee, eeee-eeeeeeee eeeeeee eee 8,8-eeeeeeeee eeee eeeeeeeeeeeeee.[888] Mee eeeeeee, eee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeeeeee eeee eeeeee–eeeeeeeeeeeeee ee eeeeeee eeeeeeeee ee eeeeeeeeeeeeeee 88 (M8 = Me), eeeeeeee ee eee eeeee-eeeeeeeee eeeeeeee eeeeeeeee, eeeee eee eeeeeeeeeeeee (M)-eeeeeee, eeeeeee eeeeeeeeeeeeee/88 (M8 = Me) ee eeeeeee ee −88 °M eeeeeeee eee (M)-eeeeeee ee 88% ee. Meee eee eeeeeeee 88 ee eeeeeee ee eeeeeeeeee eee eeeeeeeeeee ee 88 (M8 = Me) ee e Meeeeee eeeeeeeee, eeeeeeeeee e eeeeeee ee eeeeeeeee eeeeeee eee eeee eee eeeeeeee eeeeeee ee eeeee, eee eeeeeeeee eeee eeeeeeeeeeeeee/eeee 88 (M8 = Me) eeeee eee (M)-eeeeeee.[888] Meeeeeeeeeeee 88 ee eeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeee eeee 88, eeeeeeeee ee M,M-eeeeeeeeeeeeee, eeee eee eeeee ee eeee ee ee eeeeeeee ee eee eeeeeeeee. Meeee eeeeeeee, e.e. eeeeeeeee,[888] eeeeeeee,[888,888,888] eeeeeeeeeeeeeeeeeeee,[888] eee eeeeeeeeeeee eeeeeeeee,[888] eeee eeee eeee eeeeeee ee eeeeeee eeeee ee eeeeeeeeee eee eeeeeeeee eeeeeee ee eeeee.
Mee M-eeeeee-eeeeeeeeeee eeeeeeee 88 (M8 = Me) eee eeeee eeee eeeeeeeeeee M-eeee eeeeeeeee eeeeeeee eeee eeeeeeeeeee eeeee ee eee eeeeeeee eeeeee eeee ee eeee eeeeeeeeeee ee eee eeeeeeeee ee eeeeeeee-eeeeeeeee eeeeeee,[888] eeee eeeeeee eeee eee eeeeee eeee eeeee eeeeeeee eeee eee M-eeeeeeeeeeeee eeeeeeee. Meeeeeeee eeeeee ee e eeeeeeeeee eeeeeee ee eeeeeee, eeeeeeeee M-eeeeeeeeeeeeeeeeeeeeeee [e.e., 88 (M8 = MMe) eee 88], eeeeeee eeeee eeeeeeeee, eeee eee ee eeee ee eeee.[888,888,888,888–888]
Meeeeee eeeeeeeeeee 8,8-eeeeeeeeeeeeeeee eeeeeeeeeee, eeee ee eeeeeee-[888,888] eee eeeeee-eeeeeeeee[888] eeeeeee, eeeeeeeee-eeeee eeeeeeeeee,[888,888] eee eeeeeeee eeeeeeee,[888] eeee eeee eeeeeeeee ee eeeeeeeeee eeeeeeeeeeee (Meeeee 88). Meeeeeeeee, eee eeeee eeeeee eeeeee M-eeeeeeeeee eeeeeeeeeeeeeeee 88, eeeee eeeeee eeee eee eeeeeeeeeeeeeee eeee, eeeeeeee eeee eeeeeeeeeee ee eee eeeeeeeee ee 8-eeeeee- eee 8-eeeeeeeeeeeeeeeeee.[888] Mee eeeeeeeee M-eeeeeeeeee eeeee eeeeeee 88 eeeeeeee e eeeeeeeeeee eee eeeeeeeee eeeeeeee ee 8 eee% eeeeeee eee eee eeeeeeeee ee eeeee eeee eeeeeee eee a-eeee eeeeeee.[888] Mee eeeeeeeeeeee-eeeeeee eeeee eeeeeee 88[888] ee eeeeeeeeee eee eeeeeeeeeee ee eeeeeee-eeeeeeeee eeeeeeeeeeeeeeee eeeeeeeee ee Meeeee.[888,888] Meeeeee eeeeeeeeeee ee eeeeeeeeeee, eeeeeeeeee eeeeeeeee eeee ee eeee ee eeeeeeee ee eeeeee eeeeeeeee.
Meeeee 88 Meeeeeee Meeeeeeeeee 8,8-Meeeeeeeeeeeeeee Meeeeeeeeee[888,888,888]
Meeeee–eeeeeeeeeeeeeee, eeeeee–eeeeeeee eeeeeee eeeeeee, eee eee eeee eeeeeeee eeeeeeeeeeeeee eee eee eeee eeeeee eeeeee eeeeeeee eeee ee eeeeeeeeeeeeeee-eeeeeeeee eeeeeeeee ee eeeeeee. Meeeee–eeeeeeeeeeeeeee ee eee eeee eeeeeeee eee ee eeeee eeee ee 8 °M. Mee eeeeeeeeee eeeeeeee, eeeeeeeeee eeee eeeeee eeeeeeeeeee, eee eeeeee eeeeeeee eeee eeeee eeeeeeeeeee eee ee eeeeeeeee eeeeeeeee ee eeeeeeeeeee. Mee eeeeeee, eeeeeeeeeeee ee eeeeeee eeee eeeeeeeeeeee eeeeee/(M)-88 (M8 = Me) ee eeeeeee 8-eeeeeeeeeeeee ee 88% ee, eeeeeee 88% ee ee eeeeeeee eeee eee eeeeeeeeee eeeeee–eeeeeeeeeeeeeee ee eeee.[888] Meeeee–eeeeeeeeeeeeeee eeeeeeeee eeeeeeeeee ee M-eeeee-M-eeeeeeeeeeeeeeee eee eee eeeeeeeeeeee eeeeeeeee, eeeeeeeeeee eee eeeeeeeeeeeee ee eeeee eeee eeeeeee eeeee eeeeeeeee eeeeeeeee eeeeeeeeeee ee eee Meeee–Meeeee–Meeeeee (MMM) eeeeeeeee.[888,888,888] Meeeee eeeeeeeee eeee eeeee eeeeee, e.e. M,M-eeeeeeeeeeeeee[888] eee M-eeee-eeeee-M-(eeeeeeeeeeeeee)eeeee,[888] eee eeee eeeeee eeeeee eeeeeee. Mee eeeeee eeeeeee, eeeee eeeeeeeeee ee eeeeeeee eeeeeeeee, eeeeeeeeee eeeeee ee eee eeeeeeeee eeeeeeee.
Mee eeee ee eeeeeeee eeeeeee ee eee eeeeeeeee eeee eeeee eeeeee–eeeeeeee eeeeeee eeeeeee eee ee eeeeeee ee eeeee eeeeeee eee eeeeee eeeeeee eeee eeeeeeee 8,8,8,8,8,8,8,8,8,8,8,8,8,8,88,88,88-eeeeeeeeeeeeeeeeeeee eeeeee eeeeeee, eeeee eee ee eeeeeeee.[888] Meeeeeeeeeeeee, e eeeeeeeeeeeeee eeeeee, ee eeee eeeeeeeee eeee eeeeee eee eee ee eeee ee eeeeeeeeeeeee eeeeeeee, eeee ee eeeeeee eee eeeeeeeeeeeeeee, ee eee eeeeeeeeeeee.[888,888,888,888,888]
Mee eeeeeeeeeeeeee eeeeeee ee eee MMM eeeeeeeee eeeeeee ee eeeeeee eeeeeee eee eee eeeeeee eeeeee ee eeeeeee eee eeeeeee eeeeeeeeeee.[888,888] Mee eeeeeeeee eeeeeee eeee eeee eeeeeee: eee eeeeeeee eeeeeeeee;[888,888,888,888,888] eee eeeeeeeee, eeeeeeeeeee, eee eeeeeee;[888,888,888,888,888] eee eeeeeeeee;[888,888,888,888,888,888] eee eeeeee eeeeee;[888,888,888,888,888,888] eee eeee eee eeeee ee eee eeeeeee eeeeeeee;[888,888,888] eee eeeeeeeeeee;[888,888,888] eee eee eeeeeee.[888,888,888]
Meeeeeeeeeeee, eee eeeeeeee eee-eee eeeeeeeeee, eeeeeeeee eeeeee eee eeeeeeee eeeeeeeeee, eee eeeeeeeeeeee, eeeeeeeeeee eeeeeeeeeeeeee eee eeeeeeee ee eee eee- eee eeeeeeee-eeeeeeeee eeeeeee. Me e eeeeeeee eeeeeeeee eeeeeeeee, eeeeee ee eeeeeeeee eeee eeeeeeeeeee/eeeeeeeeeeeeeeeeee eeeeeeeeeee, eee eeeeeeeeeeeeeee 88 (M8 = M) (8 eee%) ee eeeeeeeee ee eeee.[888] Meeeeeeeeeee, 8-eeeeeeeeeeee-8-eee, 8-eeeeeeeeeee-8-eee, eee 8-eeeeee-, 8-eeeee-, 8-eeeee-, eee 8-eeeeeeeeeeeeeeeeee eeeeeee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee (88–88% ee), eeeeeee 8-eeeeeeeee, a-eeeeee- eee a-eeeeeeeeeeeeeeeee, eee a-eeeeeee-a,a-eeeeeeeeeeeeeeeeeeee eeeee eeee eeeee eeeeeeeeeee.[888] Me eee eeeeee-eeee eeeeee, eeeeee–M,M-eeeeeeeeeeeeee eeeeeee ee eeeeeeeee eeee eeeeee eeeeeeeeeee eee eeeeeeee eeeeeee ee eee eeeeeeee ee eee eeeee ee eeee eeeeeeeeeee, eeeeeeee ee eee eeeeeeee ee (M)-8,8-eeeeeeeeeeeeeeee [(M)-88].[888]
Mee eeeeeeeee 88 eee eeeeee eeeeeeeee ee eee eeeeeeeee ee eeeee eeee eeeeeee, eee eeeeeeee ee eee eeeeeeeeeeee ee (M)-88 (M8 = Me) eee eeeeeeeee ee Meeeee 88.
Meeeee 88 Meeeeeeee ee Meee Meeeee Meeeeee eeee Meeeee/M-Meeeeeeeeeeeeeeeeeeee Meeeeeee[888,888,888,888,888,888,888]
Meeeee eeee eeeeeee, eeee ee eeeee-8-eee, eee eeeee e eeeeeeee eeeeeeeee eeeeeeeee ee eeeeeeeee,[888] 8-eeeeeeeee,[888,888,888,888] eeeeeeeeeeeeee eeeeeee,[888,888,888,888,888] eee eeeeee eeeeeeeeeeeeee eeeeeee[888] eee eeeeeeeeeee eeeeeee eeee eeeeee/(M)-88 (M8 = Me). Meeeee eeeeeeeeee eeeeeee eee eeee eeeeeeeee ee eeeeee eeeeeeeeeee ee eeee eeeee, eeeeeee eeeeeeeeeeeee eeeeeeee. Meeeeeeeeeee, eeeeeeee ee 88–88% ee eeee eeee eeeeeeee, eeee eee MMM eeeeeeeee eeeee eeeeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeee eeeeeeeeeeeee eee eeeeeeeee eeeeeeeeeeeeeee, eeeee eee eeee eeeeee eeeeeeeee eeee ee eee eeee.[888] Meeeeeeee eeeeeee eeee eeeeeeeeee eeeeeeeee eeeeee, eeee ee eeeee eeeeee eeeeeee (eeeee = eMe, e-Me, Me), eee eeeeeee eeeeeeeeeee eeee eeeeee–M,M-eeeeeeeeeeeeee/(M)-88 (M8 = Me), eeeeeeeee eee eeeeeeeeeeeee eeeeeeee ee 88, 88, eee >88% ee, eeeeeeeeeeee.[888] eee-M-Meeeee-8-(eeeeeeeeeeeee)-8-eeeeeeeeeeeeeeeeeeeee ee eeee eeeeeeeee ee eee eeeeeeeee ee eeeeeeeeee eee eeee-eeeee eeeeee eeeeeee.[888] Meeeeee eeeeeeeee eeeeeeeee eeeeeee eeee eeee eeeeeee eeee eeeeee/eeeeeeeeeeeeeee eeeeeeeee eeee eee eeeeee eeeeeee 88, ee eee eeeeeeee ee 8-eeeeeeeeee, eeeeeeeee eeeeeeee ee 88–88% ee (Meeeee 88).[888]
Meeeee 88 Meeeeeeee ee Meeeeeeee Meeeeee eeee Meeeee/Meeeeeeeeeeeeee Meeeeeeee eeee e Meeeee Meeeeee ee eee Meeeeeee ee 8-Meeeeeeeee[888]
e Me eeeeeeeeeeee eeeeee ee 88% eee eeeeeeee eeee eee eeeeeeee eee eeeeeeeee ee 88 °M.
M eeeeeeeeeee ee −88 °M ee eeeeeee eee eee eeeeeeeee ee eee eeeeeee eeeeeee, eeeeee eeeeeeeeee eeeeee eeeeee, eee eee eeeeeeeeeee eeeeeeeee ee eeeee eeeeeeeeeee. Mee eeeeeeeee eee eeee ee eeeeeee eee ee eeeeeee eeeee, eeeeeee, ee eeeeeeeeeeeeeee eeee eeeeeeee eeeee eeeeeeeeeee. Me eeeeee ee eeeee eeee eee eeeeeeeee ee 8-eeeeeeeeeee-8-eee, ee eeee eeeeeeeeeee ee eee eeeeeeee ee eeeeeee ee 8-eeeeeeeeee, eeeeeee (M)-8-eeeeeeeeeee-8-ee, ee 88 eee 88% ee, eeeeeeeeeeee.[888]
References
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
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