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Asymmetric Cyclization of α‐Silyl Esters to Give Functionalized Hydrindanones
Author(s) -
Schinzer Dieter,
Blume Thorsten,
Jones Peter G.
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199625001
Subject(s) - alicyclic compound , aldol reaction , silylation , chemistry , intramolecular force , organic chemistry , catalysis
Desilylations can trigger the intramolecular aldol reaction of alicyclic tricarbonyl compounds. Ester enolates are formed selectively and cyclize to give functionalized hydrindanones [Eq. (a); R 1 = (−)‐menthyl, (−)‐ and (+)‐phenylmenthyl; SiR 3 SiMe 3 , SiPh 2 Me]. The cyclization products are extremely important and useful synthetic building blocks for the synthesis of steroids.