Welcome to LookChem.com Sign In|Join Free

Article Doi

Chemistry of Silylketenes: a Simple Preparation of α-Silyl-α-stannylacetic Esters and Their Stereoselective Reformatsky-type Reaction with Aldehydes or Aldimines

DOI: 10.1039/P19920002813

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2813 - 2820 (1992)

Update date:2022-08-04

Topics:

Authors:

Akai, ShujiAkai, Shuji

Tsuzuki, YasunoriTsuzuki, Yasunori

Matsuda, SatoshiMatsuda, Satoshi

Kitagaki, ShinjiKitagaki, Shinji

Kita, YasuyukiKita, Yasuyuki

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19920002813

Silylketenes 1a, b reacted smoothly with alkoxystannanes 3 to give the corresponding α-silyl-α-stannylacetates 4 almost quantitatively.Treatment of 4 with TiCl4 caused selective cleavage of the C-Sn bond to bring about Reformatsky-type reaction with aldehydes 6 giving β-hydroxy-α-silyl esters 7.These two steps were carried out by one-pot operation, and variously substituted compounds 7 were obtained with high syn-selectivity (52-<*>96percent d.e.) in 41-89percent yields.A similar one-pot procedure starting from 1a-c, 3, and aldimines 11 also provided the corresponding β-amino-α-silyl esters 12 with excellent syn-selectivity (<*>96percent d.e. ) in 64-94percent yields.Stereocontrolled preparation of both (E)- and (Z)-α,β-unsaturated esters 8 and a syn-amino diol derivative 17 from syn-7 and syn-12, respectively, is also described.

View More

Products guided by the article

Product name:3-pentyl (2R*,3S*)-2-(tert-butyldimethylsilyl)-3-hydroxy-3-phenylpropionate

Cas No:138964-25-7

138964-25-7

R&D Labs maybe for 138964-25-7

Relevant to this article

Hot Product