Catalytic enantioselective synthesis of (-)-Prostaglandin E1 methyl ester based on a tandem 1, 4-Addition-Aldol reaction

…, R Naasz, AJ Minnaard, BL Feringa

Index: Arnold, Leggy A.; Naasz, Robert; Minnaard, Adriaan J.; Feringa, Ben L. Journal of Organic Chemistry, 2002 , vol. 67, # 21 p. 7244 - 7254

Full Text: HTML

Citation Number: 82

Abstract

Catalytic enantioselective 1, 4-additions and tandem 1, 4-addition-aldol reactions of dialkylzinc reagents to cyclopentene-3, 5-dione monoacetals in the presence of an in situ generated Cu (OTf) 2/chiral phosphoramidite catalyst result in highly functionalized cyclopentane building blocks with ee's up to 97%. A new synthesis of cyclopentene-3, 5- dione monoacetals is presented as well as its use in a tandem 1, 4-addition-aldol protocol ...