HIGH-PRESSURE ALLYLSTANNANE ADDITION TO ALPHA-AMINO ALDEHYDES - SYN DIASTEREOSELECTIVITY IN THE ABSENCE OF CHELATION CONTROL

Authors
COKLEY TM ISAACS NS MCCLUSKEY A YOUNG DJ
Citation
Tm. Cokley et al., HIGH-PRESSURE ALLYLSTANNANE ADDITION TO ALPHA-AMINO ALDEHYDES - SYN DIASTEREOSELECTIVITY IN THE ABSENCE OF CHELATION CONTROL, Silicon, germanium, tin and lead compounds, 20(9), 1997, pp. 581-582
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Silicon, germanium, tin and lead compounds → ACNP
ISSN journal
07921241
Volume
20
Issue
9
Year of publication
1997
Pages
581 - 582
Database
ISI
SICI code
0792-1241(1997)20:9<581:HAATAA>2.0.ZU;2-Z
Abstract
Contrary to expectations, the high pressure (9 kbar, 30 degrees C) med iated addition of allyltrimethylstannane (2) to alpha-amino aldehydes (1) proceeds via an anti - Felkin - Anh mode to provide predominantly (60 - 88%) syn homoallylic alcohols. The diastereoselectivity of this reaction is dependent on the amino aldehyde side chain.