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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.

Highly Diastereoselective Addition of Grignard Reagents to N-Glyoxyloyl-(2R0-bornane-10,2-sultam-Comparative Studies

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

Polish Journal of Chemistry

2002

Vol. 76 / nr 11

1595-1600

N-Glyoxyloyl-(2R)-bornane-10,2-sultam (3), readily prepared from (2R)-bornane-10,2- sultam (1), was used in the Grignard reaction with methylmagnesium bromide (4a), phenylmagnesium chloride (4b), benzylmagnesium chloride (4c), allylmagnesium chloride (4d), and vinylmagnesium bromide (4e). Reactions of 3 with Grignard reagents 4a-d led to the desired adducts 5 with predominance of the (14S)-diastereoisomer. The reaction of 3 with vinylmagnesium bromide (4e) failed to give the adduct of type 5. Stereochemical models for the reactions studied are proposed.