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Desymmetrization of Prochiral Phosphanes Using Derivatives of (−)‐Cytisine
Author(s) -
Johansson Magnus J.,
Schwartz Lennart O.,
Amedjkouh Mohamed,
Kann Nina C.
Publication year - 2004
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.200400006
Subject(s) - sparteine , chemistry , alkyl , deprotonation , desymmetrization , organic chemistry , cytisine , aryl , stereochemistry , medicinal chemistry , enantioselective synthesis , catalysis , ion , biochemistry , receptor , nicotinic agonist
Historically, (−)‐sparteine· sec ‐BuLi has been used to desymmetrize prochiral phosphanes. In this report, derivatives of an alkaloid extracted from the seeds of Laburnum anagyroides have been utilized to mimic (+)‐sparteine, which is not readily available. In several cases, the enantioselectivities achieved with the (+)‐sparteine surrogates outperformed (−)‐sparteine itself in the deprotonation of alkyl‐substituted (as well as aryl‐substituted) prochiral phosphane derivatives. In addition, use of these surrogates allows a new methodology for a chiral switch in phosphorus chemistry. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)