Catalytic asymmetric synthesis of syn-aldol products from intermolecular C-H insertions between allyl silyl ethers and methyl aryldiazoacetates

Authors
Davies, HML Antoulinakis, EG Hansen, T
Citation
Hml. Davies et al., Catalytic asymmetric synthesis of syn-aldol products from intermolecular C-H insertions between allyl silyl ethers and methyl aryldiazoacetates, ORG LETT, 1(3), 1999, pp. 383-385
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
3
Year of publication
1999
Pages
383 - 385
Database
ISI
SICI code
1523-7060(19990812)1:3<383:CASOSP>2.0.ZU;2-U
Abstract
[GRAPHICS] Rh-2(R-DOSP)(4)-catalyzed decomposition of methyl aryldiazoacetate in the p resence of allyl silyl ethers results in a regioselective C-H insertion; Th e resulting beta-siloxy esters are formed with high enantioselectivity (74- 92% ee) and diastereoselectivity (96-98% de) when trans-disubstituted allyl silyl ethers are used as substrates.