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Preparation and evaluation of N-sulfinyl dienophiles for asymmetric hetero-diels-alder reactions

✍ Scribed by Molla Mellese Endeshaw; Lars K. Hansen; Odd R. Gautun

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
812 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A series of N‐sulfinyl dienophiles 1c‐i has been screened in asymmetric hetero‐Diels‐Alder reactions using chiral bis(oxazoline)copper(II) and ‐zinc(II) triflates. The survey pointed out N‐sulfine 1c (R  P(O)(OPh)~2~) as the most promising N‐sulfine regarding yield and stereoselectivity (up to 97% ee). The relative configurations, and in one case the absolute configuration, of the HDA adducts were established by X‐ray analysis.

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