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- Title
Enantioselective Phase-Transfer Catalytic α-Benzylation and α-Allylation of α- tert-Butoxycarbonyllactones.
- Authors
Ha, Min Woo; Lee, Heejin; Yi, Hye Yeong; Park, Yohan; Kim, Sori; Hong, Suckchang; Lee, Myungmo; Kim, Mi ‐ hyun; Kim, Taek ‐ Soo; Park, Hyeung ‐ geun
- Abstract
A new enantioselective α-benzylation and α-allylation of α- tert-butoxycarbonyllactones was devloped. α-Benzylation and α-allylation of α- tert-butoxycarbonylbutyrolactone and α- tert-butoxycarbonylvalerolactone under phase-transfer catalytic conditions (50% cesium hydroxide, toluene, −60 °C) in the presence of ( S, S)-3,4,5-trifluorophenyl-NAS bromide (1 mol%) afforded the corresponding α-substituted α- tert-butoxycarbonyllactones in very high chemical yields (up to 99%) and optical yields (up to 99% ee). The synthetic potential of this method has been successfully demonstrated by the asymmetric synthesis of unnatural α-quaternary homoserines, 3-alkyl-3-carboxypyrrolidine and 3-alkyl-3-carboxypiperidine.
- Publication
Advanced Synthesis & Catalysis, 2013, Vol 355, Issue 4, p637
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201200976