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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.

The Use od Furan Derivatives in Asymmetric Synthesis and Transformation

Jurczak J., Kobrzycka E., Raczko J.

Polish Journal of Chemistry

1999

vol. 73 nr 1

29-41

Asymmetric synthesis of furyl alcohols and amines, as well as kinetic resolution of racemic mixtures of furylcarbinols are described. Some examples of asymmetric alkylation of furan derivatives and preparation of butenolides are also presented.