Chen, S;Salo, EC;Wheeler, KA;Kerrigan, NJ

2012

April

Organic Letters

BINAPHANE-Catalyzed Asymmetric Synthesis of trans-beta-Lactams from Disubstituted Ketenes and N-Tosyl Arylimines

Published

35 ()

HUMAN CYTOMEGALOVIRUS PROTEASE STEREOSELECTIVE-SYNTHESIS IMINES NUCLEOPHILE KETOKETENES INHIBITION TANDEM

14

1784

1787

The development of a BINAPHANE-catalyzed formal [2 + 2]-cycloaddition of disubstituted ketenes and inexpensive N-tosyl arylimines that provides access to a variety of highly substituted beta-lactams (16 examples) is described. The BINAPHANE catalytic system displays moderate to excellent enantioselectivity (up to 98% ee) and high diastereoselectivity in most cases, favoring formation of the trans-diastereomer (13 examples with >= 90:10).

WASHINGTON

1523-7060

10.1021/ol3003783