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Aldol reactions of methyl (2-tributylstannyl)tetrahydrofuran-3-ylcarboxylate lithium enolate

✍ Scribed by Roy L. Beddoes; Mark L. Lewis; Peter Quayle; Yuekun Zhao; Michael Attwood

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
281 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis

The al&l reactions and subsequent &znsrnetallarion of ~skannylpropionates is described.

We recently reported' that the lithium enolate (2) undergoes clean alkylation reactions generating the stannanes (3) with high levels of asymmeaic induction (d.s. > 99:5). The stannanes (3) serve as useful intermediates for the stereoselective synthesis of 2,3,3+risubstituted tetrahydrofuransl as outlined in Scheme 1.

As a continuation of our studies in this area we wish to report our intial results concerning the aldol reactions of the enolate (2).

πŸ“œ SIMILAR VOLUMES

Stereoselective alkylation of methyl (2-
Stereoselective alkylation of methyl (2-tributylstannyl)tetrahydrofuran-3-ylcarboxylate lithium enolate:- Access to 2,3,3-trisubstituted tetrahydrofurans
✍ Yuekun Zhao; Roy L. Beddoes; Peter Quayle πŸ“‚ Article πŸ“… 1994 πŸ› Elsevier Science 🌐 French βš– 134 KB

## 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