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Zeh, J.; Hiersemann, M., Science of Synthesis: Stereoselective Synthesis, (2011) 3, 353.
The Claisen rearrangement usually requires high temperature or catalysis by a π- or σ-Lewis acid, and therefore may not be applicable to substrates with sensitive functional groups. The allyl vinyl ether can be generated with a defined configuration of either double bond in situ or in a separate step that precedes the rearrangement.
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Meeeee 8 Meeeeee Meeeeeeeeeeee ee eee Meeee Meeeeeeee ee (+)-Meeeeeeeeeee[88]
Me eeeeeee ee e Meeeeee eeeeeeeeeeeee eeee eeeeeeee eee e eeee-eeee eeeeeeeeee-eeeee eeeeeeeee ee eeeeeeee ee Meeeee 8.[88] Meeeeee ee eee eeeeeeee eeeeee ee eee eeeeeeeee eeeeeeeeee-eeeee eeeeeeeee 88, eeeeeeeeeeeee eeee eeeeeeeeeeee eee eeeeeeee eee eee eeeeeeeeeeeee. Meeee, ee ee eeeeeeee ee eeeeeee eee eeeeeeeeeeeee eee eeeee eeeee eeeee 88 eeee eee eeeee 88, eee eee eeeee 88, eeeeeee eeeeeeeeee eeee eeeeeeeeeeeee. Meeeeee, eee Meeeeee eeeeeeeeeeeee eeeeeeee eeee e eeeeeeee eeeeeeee ee eeeeeeeee eeee eee eeeee eeeee eeeee 88 ee eee eeeeeeeeee eeeeeeeee eeeee[8.8]eeeeee 88. Meeeeeeeee eeeeeeeeeeeeeee eeeeee eee eeeeeeeeeeeee eeeeeee eeeeeee (−)-eeeeeee (8).
Meeeee 8 Meeeeee Meeeeeeeeeeee ee eee Meeee Meeeeeeee ee (−)-Meeeeee[88]
Mee eeeeeeeee eeeee eeeee 88, eeeee ee eeeeee ee eeee eeeeeeeeeee, eee eeeeeeee ee e eeeee eeeeeeeee ee (±)-eeeeeeee eeee (8) (Meeeee 88).[88] Meee(M)-eeeeeeeee eeeeeeeeeeeee ee eeeee 88 eeeeeeee ee eeeeeeeee eeeee eee eeeeeee eeeeeee 88, eeeee eeeeeeeeee eeeeeeee eee eee eeeeeeeeee eeeee 88, eeee eeeeeeee eeeeeeeeeee (ee 88:88). Meeeeeeee eeeeeeee ee eeeeeee eeeeeee 88 eeeeeeee eee eeeeeeeeeee 88, eeeee eeeeeeeee e eeeeeeeee(8)-eeeeeeeee eeeeeee eeeeeeeeeee ee eeeeee eee eeeeeeeeeee eeeeeeeee 88 ee (±)-eeeeeeee eeee (8).
Meeeee 88 Meeeeee Meeeeeeeeeeee ee e Meeeeeeee Meeee Meeee ee eee Meeee Meeeeeeee ee (±)-Meeeeeee Meee[88]
Meeeeeeeeeee Meeeeeeee
8-[(8M,8M)-8-(Meeeeeeeeeeeeeeee)-8-[(eeee-eeeeeeeeeeeeeeeeeee)eeeeee]-8-{[(8-eeeeeeeeeeeee)eee]eeeeee}-8,8,8,8-eeeeeeeeeeeeeeeee-8-ee]eeeeeee (88); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeee(MM) eeeeeee ee eeeeee eeeee eee eee ee eeeee ee eeeeeeee, eeeeeee, ee eeeeeeeee.
M eeeeeee ee eeee 88 (8.888 e, 8.88 eeee), Me(MMe)8 (8 ee, 8.88 eeee), eee Me8M (8 µM, 8.88 eeee) ee eeeee eeeee eeeee (8 eM) eee eeeeee ee 888 °M (eee-eeee eeeeeeeeeee) ee e eeeeee eeeee eeee eee 88 e. Meeeeeeeeee ee eee eeeeeeee eeeeeeee eeeeeeee ee eeeee eeeeeeeeeeeeee ee eee eeeeeee (eeeeee/MeMMe 8:8) eeee e eeeeeeeee eee; eeeee: 8.888 e (88%).
References
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