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Synthesis and Anionically Induced Domino Reactions of Chiral α‐Bromo α,β‐Unsaturated Esters
Author(s) -
Braun Norbert A.,
Bürkle Ulrike,
Feth Martin P.,
Klein Iris,
Spitzner Dietrich
Publication year - 1998
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/(sici)1099-0690(199808)1998:8<1569::aid-ejoc1569>3.0.co;2-w
Subject(s) - chemistry , diastereomer , domino , dihydroxylation , enone , sharpless asymmetric dihydroxylation , organic chemistry , enantioselective synthesis , stereochemistry , catalysis
The chiral α‐bromo α,β‐unsaturated esters 3 and 9 are prepared by asymmetric Sharpless dihydroxylation (AD) of 5 and from ester 7 and the chiral diols 8 by transacetalization, respectively. Both types of α‐bromo α,β‐unsaturated ester react with the kinetic lithium dienolates of enone 10 to give functionalized tricyclo[3.2.1.0 2,7 ]octanes 11 . Esters 3 give one single diastereomer ( de ≥ 95%), whereas mixtures of diastereomers ( de 28 to 46%) are obtained with the esters 9 .