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An Organocatalytic, δ‐Regioselective, Diastereoselective, and Enantioselective Nucleophilic Substitution of Cyclic Morita–Baylis–Hillman Alcohols with N ‐Boc‐3‐benzyl‐2‐oxindoles
Author(s) -
Qiao Zhen,
Zhong NengJun,
Zhang Tao,
Liu Li,
Wang Dong,
Chen YongJun
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201461
Subject(s) - chemistry , regioselectivity , enantioselective synthesis , nucleophilic substitution , trifluoroacetic acid , trifluoroacetic anhydride , organic chemistry , organocatalysis , vicinal , nucleophile , medicinal chemistry , catalysis , stereochemistry
Abstract A direct asymmetric substitution was developed for the reaction of cyclic Morita–Baylis–Hillman alcohols with 3‐benzyl‐2‐oxindoles that are catalyzed by a primary amine derived from alkaloids in combination with trifluoroacetic acid. The unusual δ‐products with vicinal chiral quaternary and tertiary carbon centers were obtained as the major products in yields up to 73 % with excellent diastereoselectivities (up to 99:1) and enantioselectivities (up to 98 % ee ).