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Please login or sign up for a free trial to access the full content.1.1.7.3 Ylide-Mediated Cyclopropanation Reactions
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Belderrain, T. R.; Nicasio, M. C., Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (2014) 1, 272.
The conjugate addition of an ylide to an electrophilic alkene gives an enolate intermediate from which elimination of the heteroatom-containing moiety triggers a cyclization process, rendering a cyclopropane ring. This transformation is classified as a Michael-initiated ring closure (MIRC) type reaction (Scheme 15).[1,12,15,90–94] The ylide cyclopropanations of acyclic alkenes are nonstereospecific, and both E- and Z-alkenes usually produce the trans-cyclopropane due to fast rotation around the C—C bond.
Meeeee 88 Mee Meeee Meeeeeeeeeeeeeee Meeeeeee[8,88,88,88–88]
Meeeeeeeeeeeeeeeeee eeeeeeeee [Me8M+(M)MM8−, Meeeeʼe eeeee, 88],[88] ee eee eeee eeeeeeee eeee eeeeeeeee eeeeeeee eeeeeee. a,B-Meeeeeeeeee eeeeeee eee eeeeeeeee eeeeeeeeee eee Meeee–Meeeeeeeee[88] eeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeeeeee eeeeeeeee, eeeeeeeeee eeee eeeeee ee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeee. Mee eeeeeeee eeeeeeeee eee eee Meeee–Meeeeeeeee eeeeeeeeeeeeeeee eeeeeeee eeeeeeeeeeee ee eee eeeee ee eee eeeeeeee ee eeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeeeeeeeee eeeeeeee ee eeeeee eeee eeeeee eeeeeee ee eee eeeeeeee eeeeeeeee eee 88–888 eeeeeee, eeeeeeee ee eeeeeeee ee eee eeeee eee eeeeeee eee eeeeeee ee 88 °M eee 8 eeeee.[88] Meeeeeeeeeeee ee eee eeeeeeee eeeeeeeeee eeee eeee eeeeeeeee ee eeeee ee eeeeeee eee eeeeeeee eeeee eeeee-eeeeeeee eeeeeeeeee (Meeee 8, eeeee 8)[88] ee eeeee ee eeeee eeeeee ee eeeeeee (eeeee 8).[88] Me eeeeeeeeeee eeeeeeeee ee eee ee eeeeee “eeeeeee eeeeeeeee” eeeeeeeeeeeeeeee,[88] eeeee eeeeeeee ee eee eeeeeeeee ee e eeeeeeee eeeeeeeee eeeeeeee ee eee eeeee eeee e eeeeeeee eee eeeeeeeee eeeeeee ee eeeeeeeeeee eeee eee eeee (eeeee 8). Meee eeeeeeee eeeeeeeeee eee eeeeeeeeeeee eeeeeeeeee eee eeeeeee eeeeeeee eeeeeeee eeeee (ee ee 88 eee ee 88–88 °M). Me eeeee eee eee ee eeeeee eeeeeeeee eeeee, e eeeee eeeeeeeee eee eeee eeeeeeeee eeeee eeeeeee ee eeeeeee eeee (eeeeeeeeeeee eeeeeeeee eeeeeeeee eeee 8-eeeeee-8,8,8,8,8,8-eeeeeeeee-8M-eeeeeeee[8,8-e]eeeeeeeeee, MMMM) ee eeeeeeee eeeeeeeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeeeeeeeeeeee eeeeee ee eeeeeeeeeeee ee eee eeeeeee (eeeee 8).[88] Mee eeeeeeeeeeee ee eeeeeeeee eeeeeeeee eee eee Meeee–Meeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeee, ee eeeee eeeeeeeee, ee eeee eeeeee(8-eeeeeeeeeeeeeeeee)eeeeeeeee (88) eee eeeeeeeeeee ee Meeee 8.[88–88]
Meeee 8 Meeeeee Meeeeeeeeeeee ee eee Meeee–Meeeeeeeee Meeeeeeeeeeeeeee ee Meeeeeee[88–88]
e (eeee)MM8 = 8-eeeee-8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeee.
e MMMM = 8-eeeeee-8,8,8,8,8,8-eeeeeeeee-8M-eeeeeeee[8,8-e]eeeeeeeeee.
Meeeeeeeeeeeeeeee eeeeeeeee[88] (Me8M+MM8−) eee eeee eeee eeee ee e eeeeeeeeeeee eeeeeeeee eeeeeeee eeeeeee eee eee eeeeeeeee ee eeeeeeeeeeeee. Me ee eeeeeeeeeee ee eeee eeee eeee eeeeee eeeee eeeeee eeee eeeeeeeeeee eeeeeee ee eeeeeeee eeeeeeee eeeeeee ee eee eeeeeeee eeeeeeeeeee eeeeeeeeeee.
Mee Meeee–Meeeeeeeee eeeeeeeeee ee a,B-eeeeeeeeeee eeeeeeee eeeeeeeee eeee eeeeeeeeeee eeeeeeeeeee eeeee Meeeeʼe eeeee 88 eee eeee eeeeee eeee ee eeeeeee eeeeeeeee. Meeeeeee eeeeeeee eeee eeeeeeeee eee eeee eeeee ee eeee eeeeeeeeeeeeee eee eeeeeeeee ee Meeee 8.
Meeee 8 Meeee–Meeeeeeeee Meeeeeeeeeeeeeee ee Meeeeeee a,B-Meeeeeeeeee Meeeeeee Meeeeeeee eee Meeee Meeeeeeeee[88,88–888]
Me 8888, e eeeeee eeeeeeee eee eeeeeeeee eeee eeeeeeee e eee-eee Meeeeeeeeee eeeeeeeeeeee/Meeee–Meeeeeeeee eeeeeeeeeeeeeeee eeeeeee eeeeeeeeeeeeeeeee eee eeeeeeeee eee eee eeeeeeeeeee ee eee eeeeeeeee ee (±)-eeeeeeeeee (88) (Meeeee 88).[888]
Meeeee 88 Mee-Meee Meeeeeeee ee (±)-Meeeeeeeee eee e Mee-Mee Meeeeeeeeee Meeeeeeeeeee/Meeee–Meeeeeeeee Meeeeeeeeeeeeeee Meeeeeee[888]
Meeeeeeeee eeeeeeee ee eee eeeeee eeeee eeeeeeeeeeeeeeee eeee eeee eeee eeeeeeeee.[88,88,88] Meeeeeeee ee eee eeeeeee eee ee eeeeeee eeeeee ee eeeeeeeee e eeeeee eeeeeeeeeee ee ee eeeee e eeeeee Meeeeee eeeeeeee. Meeeeeee eeeeeeeeee eee eee ee eeeeee eeeeeeeee eeeeeeee eeeeeeee eee eeeeee. (M)-(Meeeeeeeeeeee)(8-eeeee)eeeeeeeeeee eeeeeeeee (88)[88] eeeeeee eeeeeeeee eeeeee eeeeeeeeeeeee eeeeeeeeeeeee eeee eeeeee ee eeeeeeee eeeeee eee eeee eeeeee eeeeeeeeeeeeeeeeeeee (Meeeee 88). Meeeeeeee (M)-eeeeeeeeeee 88 eeeeee eeee eeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeeeeee eeee eeeeeeeee eeeeeeeeeeeeeeeeeeee (ee 88:8) eee eeeeeeeeeeee eeeeee (88%).[888] Mee eeeeeeee ee eeeeee eeeeeeeee eeeee 88 eeee ee a,B-eeeeeeeeeee eeeee eeeee e eeeeeeeeeeee eeeeeeeeee ee 88% eeeee eee eeee eee eeeeeeeeeeee eeeeee.[888]
Meeeee 88 Meeeee Meeeeeeee Meeeeeee Meeeeeee[88,888,888]
Meeeee Meeeeee eeeeeeeee eeee ee eeeeeeeeee eeeeeeeeeeeeeeee eeee Meeeeʼe eeeee 88 eeeeeee eeeeee eeeeeeee eeeeeee,[88,88] eee eeeeee eeeee eeeeeeeeee.[88] Me eeeeeee ee eee eee ee e eeeeee eeeeeeee ee eeeeeee Meeee–Meeeeeeeee eeeeeeeeeeeeeeee ee eeeeee eeee eeeeeeeeeeeeeeeeeee eeeeeeeee (88) eee eeee eeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee Meeeeeeeee Meeeeeeeeeeeeeee ee ee Meeee eeee Meeeeʼe Meeee[88]
Meeeeeeeeeee Meeeeeeee
eeeee-Meeeee(8-eeeeeeeeeeeeeeeee)eeeeeeeee (88); Meeeeee Meeeeeeee:[88]
M eeee ee eee eeeee 88 eee eeeeeeee eeeee M8 eeee MeM (8.888 eee), eeeeeeeee(eee)eeeeeeeee eeeeee (8.88 e, 8.888 eee), eee MMMM (88 eM). Mee eeeeeee eee eeeeee ee e eeee eeeee eeee (ee. 88 °M) eee e eeee ee eeeeeeee (8.88 e, 8.88 eee) ee MMMM (88 eM) eee eeeee eeeeeee eeee eeeeeeee. Meeee 8 eee, eee eeeee eeee eee eeeeeee eee eeeeeeee eee eeeeeeeee ee ee eee 8 e, eee eeee ee 88 °M eee 8 e. Mee eeeeeee eee eeeeee eeee eeee M8M (888 eM) eee eee eeeeeee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeeee eeee eeeeee eeee M8M (8 ×) eee eeee eee. MeMe eeee, eeeee (Me8MM8), eee eeeeeeeeeeee ee eeee e eeee eeeeee eee (8.8 e), eeeee eeeeeeeeee eeeee eeeeeeee ee ee eee e eee eeeee. Mee eeeee eee eeeeeeeeeeeeeee [Meeee eeeeeee (88 e), eeeeeee (MMMMMMM:eeeeeeeeee)/eeeeeee 88:88]. Mee eeeee eeeeeeee, eeeee eee eee eeeeeee eeeeeeeeeeee, eeeeeeeee e eeeeeeeee eee (ee. 88 ee) eeeee eeeeee eeee eeee eeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeeee. Meeee eeeeeeeeee eeeeeeeee eeeeeeeee eeeeee eeeeeeeee eeee eeeee eeeeeeee eeeeeee eeee eeeeeeeee eee eeeee eeeeee eeeeeee eeeeeeee eeeeeeeeee ee 8.88 µ. Mee eeeeeeee eeee [eeeee: 8.8 e (88.8%)] eeeeeeeeee eeeee eeeeeeee ee e eeeeeeeeeeee, ee eeee eee eeeeeee ee e eeeee, eeeeeeeeeee eeeee; ee 88–88 °M. M eeeeee eeeeeeeeeeeeee eeeee [eeeeeeeee eeeee (ee 88–88 °M)] eeee eeeeeeeee eeeeeee (ee 88.8–88 °M), eee eeeeeeee eee e eeeeeee ee eeeeeee.
References
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