Enantioselective Diels-Alder reaction with an alpha-chloronitroso dienophile derived from 5-O-acetyl-2,3-isopropylidenedioxy-D-ribose

Authors
Defoin, A Joubert, M Heuchel, JM Strehler, C Streith, J
Citation
A. Defoin et al., Enantioselective Diels-Alder reaction with an alpha-chloronitroso dienophile derived from 5-O-acetyl-2,3-isopropylidenedioxy-D-ribose, SYNTHESIS-S, (12), 2000, pp. 1719-1726
Citations number
56
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
12
Year of publication
2000
Pages
1719 - 1726
Database
ISI
SICI code
0039-7881(200011):12<1719:EDRWAA>2.0.ZU;2-O
Abstract
Crystalline 5-O-acetyl-2,3-isopropylidenedioxy-D-ribonolactone oxime (8) wa s synthesised from D-ribose in 40% overall yield. The chloronitroso dienoph ile 3b was obtained from 8 by oxidation with t-BuOCl and underwent asymmetr ic Diels-Alder reaction with cyclic and acyclic dienes 10-13 to give crysta lline adducts 14a-17a in good yield and excellent enantiomeric excess (93-9 9%).