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

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.

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Bibliographische Detailangaben
Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2003-01 (20), p.2550-2551
Hauptverfasser:	Gridley, Jonathan J, Coogan, Michael P, Knight, David W, Malik, K M Abdul, Sharland, Christopher M, Singkhonrat, Jirada, Williams, Siân
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkenes - chemistry Alkynes - chemistry Amino Acids - chemical synthesis Amino Acids - chemistry Esters - chemistry Glycine - analogs & derivatives Glycine - chemistry Organotin Compounds - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	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.
ISSN:	1359-7345 1364-548X
DOI:	10.1039/b306291k