Desymmetrization of Prochiral Phosphanes Using Derivatives of (−)‐Cytisine | Zendy

Johansson Magnus J. | Zendy; Schwartz Lennart O. | Zendy; Amedjkouh Mohamed | Zendy; Kann  Nina C. | Zendy

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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)

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