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

• Autorzy: Raszplewicz K. , Sikorska L. , Kiegiel K. , Jurczak J.
• Języki publikacji: EN

Abstrakty

EN

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.

Słowa kluczowe

EN

Grignard reaction; asymetric synthesis; diastereoselection; chiral auxiliary

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 11
• Strony: 1595--1600
• Opis fizyczny: Bibliogr. 12 poz., rys.

Twórcy

autor

Raszplewicz K.

• Department of Chemistry, Warsaw University, 02-093 Warsaw, Poland

autor

Sikorska L.

• Department of Chemistry, Warsaw University, 02-093 Warsaw, Poland

autor

Kiegiel K.

• ---

autor

Jurczak J.

• Department of Chemistry, Warsaw University, 02-093 Warsaw, Poland
• Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland

Bibliografia

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