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Synthesis 2006(18): 3111-3121
DOI: 10.1055/s-2006-950194
DOI: 10.1055/s-2006-950194
PAPER
© Georg Thieme Verlag Stuttgart · New York
Enantio- and Diastereoselective Synthesis of Tetrahydrofurochromenes by Sequential Asymmetric Homoaldol Reaction and a Mukaiyama-Type Tetrahydrofuran Cyclization
Further Information
Publication History
Received
10 April 2006
Publication Date:
15 August 2006 (online)


Abstract
Herein, we report on a flexible strategy for the stereoselective construction of highly substituted tetrahydrofurochromene derivatives by Mukaiyama-type cyclizations of enantioenriched enol carbamates with O-protected salicylaldehydes. The chromenes are generated as pure diastereomers and under complete chirality transfer.
Key words
heterocycles - homoaldol reaction - lithiation - salicylaldehydes - stereoselective synthesis