New general sulfinylating process for asymmetric synthesis of enantiopure sulfinates and sulfoxides.
[reaction: see text] A general process for the efficient synthesis of sulfinyl transfer agents has been developed using cinchona alkaloids quinine and quinidine as chiral auxiliaries. The importance of these new and unique sulfinyl transfer agents is exemplified by the expedient synthesis of several sulfoxides in excellent enantiopurities and high yields.
Lu
Bruce Z
BZ
Chemical Process R&D, Sepracor, Inc., 84 Waterford Drive, Marlborough, Massachusetts 01752, USA. zlu@rdg.boehringer-ingelheim.com
Jin
Fuqiang
F
Zhang
Yongda
Y
Wu
Xinhe
X
Wald
Stephen A
SA
Senanayake
Chris H
CH
D002625:Chemistry, Organic / Q000379:methods; D002930:Cinchona Alkaloids / Q000737:chemistry*; D015394:Molecular Structure; D011802:Quinidine / Q000737:chemistry; D011803:Quinine / Q000737:chemistry; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000032:analysis / Q000138:chemical synthesis*; D013454:Sulfoxides / Q000032:analysis / Q000138:chemical synthesis*
D002930:Cinchona Alkaloids; D013441:Sulfinic Acids; D013454:Sulfoxides; D011803:Quinine; D011802:Quinidine