ASYMMETRIC HETERO-DIELS-ALDER ADDITION OF 1-METHOXYBUTA-1,3-DIENE TO (2R)-N-PYRUVOYL- AND (2R)-N-(PHENYLGLYOXYLOYL)BORNANE-10,2-SULTAM

Authors
KIEGIEL J CHAPUIS C URBANCZYKLIPKOWSKA Z JURCZAK J
Citation
J. Kiegiel et al., ASYMMETRIC HETERO-DIELS-ALDER ADDITION OF 1-METHOXYBUTA-1,3-DIENE TO (2R)-N-PYRUVOYL- AND (2R)-N-(PHENYLGLYOXYLOYL)BORNANE-10,2-SULTAM, Helvetica chimica acta, 81(9), 1998, pp. 1672-1680
Citations number
57
Categorie Soggetti
Chemistry
Journal title
Helvetica chimica acta → ACNP
ISSN journal
0018019X
Volume
81
Issue
9
Year of publication
1998
Pages
1672 - 1680
Database
ISI
SICI code
0018-019X(1998)81:9<1672:AHAO1T>2.0.ZU;2-0
Abstract
Cycloadditions of 1-merhoxvbuta-1,3-diene to (2R)-N-pyruvoyl and (2R)- N-(phenylglyoxyloyl)bornane-10,2-sultam ((-)-1b and (-)-1c, resp.) und er high-pressure conditions are presented. The absolute configurations of the cycloadducts 2b,c and of their resulting reduced alcohols 3b,c are based on their X-ray analyses. The stereochemical course of these reactions is discussed and compared to the inverse diastereoselectivi ty observed for the analogous cycloaddition to (2R)-N-glyoxyloylbornan e-10,2-sultam (1a).