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Diastereoselective Addition of Grignard Reagents to Chiral alfa-Ketoimides Derived from Oppolzer's Sultam

Raszplewicz K., Sikorska L., Kiegiel K., Bałakier T., Jurczak J.

Polish Journal of Chemistry

2005

Vol. 79 / nr 12

1901-1907

Additions of various Grignard reagents to N-pyruvoyl- (3) and N-phenylglyoxyloyl- (2R)-bornane-10,2-sultam (4) under thermal and Lewis-acid catalytic conditions are studied. High diastereoselectivity was observed in these reactions, and in the case of vinylmagnesium bromide additions to -ketoimide 4 a change of direction of asymmetric induction was found.

Diastereoselective [4+2} Cycloaddition of Cyclopentadiene to N-Tosyliminoacetyl Derivatives of Chiral Secondary Alcohols

Szymański S., Marzec M., Jurczak J.

Polish Journal of Chemistry

2002

Vol. 76 / nr 6

831-837

Syntheses of five N-tosylimines of chiral glyoxylates are described. The N-tosylimines obtained were used as dienophiles in the Lewis acid-catalyzed asymmetric hetero- -Diels-Alder reaction with cyclopentadiene to afford cycloadducts with moderate diastereoisomeric excess.