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Highly Diastereoselective, Tandem, Three‐Component Synthesis of Tetrahydrofurans from Ketoaldehydes via Silylated β‐Lactone Intermediates
Author(s) -
Mitchell T. Andrew,
Zhao Cunxiang,
Romo Daniel
Publication year - 2008
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.200800235
Subject(s) - tandem , component (thermodynamics) , lactone , chemistry , combinatorial chemistry , stereochemistry , materials science , composite material , thermodynamics , physics
Like falling dominoes! A novel tandem, three‐component reaction is described that generates up to two CC bonds, one CO bond, and three additional stereocenters leading to substituted tetrahydrofuran units. This process involves a tandem Mukaiyama aldol‐lactonization/reductive cyclization and proceeds via a silylated β‐lactone intermediate. The method was applied to prepare the tetrahydrofuran fragment of colopsinol B. Py=2‐pyridyl.