(5R)-7,8/9,10-DI-O-ISOPROPYLIDENE-2,6-DIOXA-4-AZASPIRO[4,5]DECAN-3-ONE - A NEW CHIRAL SPIROOXAZOLIDIN-2-ONE DERIVED FROM D-(+)-GALACTOSE FOR USE IN ASYMMETRIC TRANSFORMATIONS

• Published in: Journal of the Chemical Society. Chemical communications no. 14; pp. 1146 - 1147
• Main Authors: BANKS, MR, BLAKE, AJ, CADOGAN, JIG, DAWSON, IM, GAUR, S, GOSNEY, GOULD, RO, GRANT, KJ, HODGSON, PKG
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 1993; Royal Society of Chemistry
• Subjects: Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Multidisciplinary; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Heterocyclic compounds; Organic chemistry; Organic compounds; Physical Sciences; Physics; Preparations and properties; Science & Technology; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; AUXILIARY; Five membered ring; Aldose; Molecular structure; Diels Alder addition; Acid catalysis; Dienic compound; Experimental study; Oxygen heterocycle; X ray diffraction; Diastereoselectivity; Stereoselectivity; Chiral auxiliary; Cyclization; Six membered ring; Vinylic compound; Bicyclic compound; Carboxamide; Carbamate; Monocyclic compound; Organic compounds; Oxygen nitrogen heterocycle; Crystalline structure
• ISSN: 0022-4936
• DOI: 10.1039/c39930001146

Starting from D-(+)-galactose, the crystalline spirooxazolidin-2-one 2 can be readily prepared in an optically pure state by a nitrene-mediated four-step sequence, and serves to control both aldol and Diels-Alder reactions with high chiral efficiency, being easy to remove after use.