In:
Zeitschrift für Naturforschung B, Walter de Gruyter GmbH, Vol. 59, No. 4 ( 2004-4-1), p. 451-467
Abstract:
A new approach to optically active N-methylamino acids is presented, relying on stereoselective reduction of N-methylisoxazolinium salts with a dioxyethyl side-chain. The diastereoselectivity of the reduction step is studied systematically, in comparison with that of respective isoxazolines. A two-step transformation of isoxazolinium salts - with NaBH 3 (OAc) and subsequent catalytic hydrogenation as well as a one-pot reduction by catalytic hydrogenation led to high (95:5 and 87:13) diastereomeric ratios of protected erythro-N-methylaminopentanetriols. The hydroxyethyl side-chain is elaborated by oxidation to afford the β -N-methylamino acid 37, exemplifying the potential of this strategy.
Type of Medium:
Online Resource
ISSN:
1865-7117
,
0932-0776
DOI:
10.1515/znb-2004-0414
Language:
English
Publisher:
Walter de Gruyter GmbH
Publication Date:
2004
detail.hit.zdb_id:
2078109-X
detail.hit.zdb_id:
124635-5
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