Highly Diastereoselective, Tandem, Three‐Component Synthesis of Tetrahydrofurans from Ketoaldehydes via Silylated β‐Lactone Intermediates | Zendy

Mitchell T. Andrew | Zendy; Zhao Cunxiang | Zendy; Romo Daniel | Zendy

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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.

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