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Chiral Induction by Elimination‐Coupled Lithium–Ene Reaction: Synthesis of (+)‐(3 R ,4 R )‐1,2‐Dihydromultifidene
Author(s) -
Deiters Alexander,
Hoppe Dieter
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990215)38:4<546::aid-anie546>3.0.co;2-#
Subject(s) - ene reaction , lithium (medication) , chemistry , medicinal chemistry , endocrinology , medicine
Cyclization of the alkadienyl carbamates 1 to the cis ‐divinylcyclopentanes 2 with high enantioselectivity and diastereoselectivity has been successfully achieved by (−)‐sparteine‐induced asymmetric deprotonation. The conversion may be described as a hybrid of a lithium–ene reaction and an S n ′ reaction.