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Stereoselective alkylation of methyl (2-tributylstannyl)tetrahydrofuran-3-ylcarboxylate lithium enolate:- Access to 2,3,3-trisubstituted tetrahydrofurans

✍ Scribed by Yuekun Zhao; Roy L. Beddoes; Peter Quayle

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 134 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73147-9

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✦ Synopsis

A stereoselective synthesis of 233 -trifunctionaiised tetrahydrofirans is described.

We have recently shown1 that deprotonation of the tram-ester (1) under conditions of kinetic control (LDA, 1.1 cq.; THF, -78 eC; 30 mins.) generates the stable enolate (2) which upon reprotonation (NH&l; -78 eC) affords the cis-ester (3) in good overall yield (66%). Scheme 1. We now wish to report that alkylation of the enolate (2) with a variety of alkylating agents (E+) proceeds rapidly at -78 eC in THF affording the alkylated tetrahydrofurans (4) in generally high yields (Table ).

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