Highly Enantiomerically Enriched Ketone Homoenolate Reagents Prepared by (−)‐Sparteine‐Mediated γ‐Deprotonation of Achiral 1‐Alkenyl Carbamates | Zendy

Seppi Michael | Zendy; Kalkofen Rainer | Zendy; Reupohl Jens | Zendy; Fröhlich Roland | Zendy; Hoppe Dieter | Zendy

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Highly Enantiomerically Enriched Ketone Homoenolate Reagents Prepared by (−)‐Sparteine‐Mediated γ‐Deprotonation of Achiral 1‐Alkenyl Carbamates

Author(s) -

Seppi Michael,

Kalkofen Rainer,

Reupohl Jens,

Fröhlich Roland,

Hoppe Dieter

Publication year - 2004

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/anie.200352966

Subject(s) - sparteine , deprotonation , chemistry , reagent , ketone , lithium (medication) , aryl , base (topology) , butyllithium , medicinal chemistry , stereochemistry , organic chemistry , ion , medicine , mathematical analysis , alkyl , mathematics , endocrinology

Homoenolate equivalents : Enantiotopos‐differentiating deprotonation of achiral 1‐alkenyl carbamates with the chiral base n ‐butyllithium/(−)‐sparteine yields configurationally stable lithium homoenolate equivalents. In a subsequent syn or anti substitution (see scheme), γ‐substituted O ‐(1‐aryl‐1‐alkenyl) N , N ‐diisopropylcarbamates are formed with high enantio‐ and diastereoselectivity.

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