Highly diastereoselective anti-aldol reactions utilizing the titanium enolate of cis-2-arylsulfonamido-1- acenaphthenyl propionate.
[reaction: see text] anti-Aldol reaction of Ti-enolate derived from cis-2-arylsulfonamido-1-acenaphthenyl propionate with representative aldehydes proceeded in excellent yield with high diastereoselectivity. Both enantiomers of cis-2-amino-1-acenaphthenol were synthesized employing lipase-catalyzed kinetic resolution as the key step.
Ghosh
Arun K
AK
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA. arunghos@uic.edu
Kim
Jae-Hun
JH
D000447:Aldehydes / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000737:chemistry*; D008049:Lipase / Q000378:metabolism; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry*
D000447:Aldehydes; D006844:Hydrocarbons, Cyclic; D011422:Propionates; D013449:Sulfonamides; D014025:Titanium; D008049:Lipase