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.
Chemistry Department, Cardiff University, P.O. Box 912, Cardiff, UK CF10 3TB.
Jonathan J
JJ
Gridley
Michael P
MP
Coogan
David W
DW
Knight
K M Abdul
KM
Malik
Christopher M
CM
Sharland
Jirada
J
Singkhonrat
Siân
S
Williams
D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D000596:Amino Acids; D004952:Esters; D009947:Organotin Compounds; D005998:Glycine