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Phthalides by rhodium-catalyzed ketone hydroacylation.

Authors
  • Phan, Diem H T
  • Kim, Byoungmoo
  • Dong, Vy M
Type
Published Article
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Publication Date
Nov 04, 2009
Volume
131
Issue
43
Pages
15608–15609
Identifiers
DOI: 10.1021/ja907711a
PMID: 19813746
Source
Medline
License
Unknown

Abstract

Phthalides are biologically relevant five-membered lactones found in herbs, fruits, and vegetables. Herein we communicate the first atom-economical approach to phthalides by using enantioselective ketone hydroacylation. In the presence of Rh[(Duanphos)]X (X = NO(3), OTf, OMs), various 2-ketobenzaldehydes undergo intramolecular hydroacylation to produce phthalide products in good yields and 92-98% ee's. Our study highlights the key role counterions play in controlling both reactivity and enantioselectivity. A concise asymmetric total synthesis of the celery extract (S)-(-)-3-n-butylphthalide is also presented.

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