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( E )‐α‐Sulfonamidocrotylboronates as Reagents for the Stereoselective Homoaldol Synthesis
Author(s) -
Schlapbach Achim,
Hoffmann Reinhard W.
Publication year - 2001
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 - 10.1002/1099-0690(200101)2001:2<323::aid-ejoc323>3.0.co;2-a
Subject(s) - chemistry , stereoselectivity , lactol , reagent , nucleophilic substitution , nucleophile , organic chemistry , substitution reaction , substitution (logic) , combinatorial chemistry , stereochemistry , lactone , catalysis , computer science , programming language
The α‐sulfonamidocrotylboronates 9 and 10 have been generated by nucleophilic substitution at the α‐chlorocrotylboronates 1b , in yields of up to 70%. The α‐sulfonamidocrotylboronates 9 and 10 react with aldehydes at room temp. and 4 kbar pressure to give the anti ‐homoallylic alcohols 13 and 14 with high simple diastereoselectivity. These latter may be directly converted into the lactol ethers 15 in a one‐pot procedure.