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A stereoselective synthesis of anti-gamma,delta-alkynyl- and -alkenyl-beta-hydroxy-alpha-amino esters from tin(II) enolates of glycinate.

Chemical communications (Cambridge, England) (2003-11-05)
Jonathan J Gridley, Michael P Coogan, David W Knight, K M Abdul Malik, Christopher M Sharland, Jirada Singkhonrat, Siân Williams
ABSTRACT

Condensations between the tin(II) enolate 11 of ethyl N-tosylglycinate and conjugated ynals 12 and ynones 14 are highly diastereoselective, in favour of the anti-isomers 13 and 15; similar reactions of enals and enones 17 show lower but still useful levels of anti-stereoselectivity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Tin(II) chloride dihydrate, ≥99.995% trace metals basis