EFFICIENT GENERAL ASYMMETRIC SYNTHESES OF 3-SUBSTITUTED 1(3H)-ISOBENZOFURANONES IN VERY HIGH ENANTIOMERIC EXCESS

Authors
RAMACHANDRAN PV CHEN GM BROWN HC
Citation
Pv. Ramachandran et al., EFFICIENT GENERAL ASYMMETRIC SYNTHESES OF 3-SUBSTITUTED 1(3H)-ISOBENZOFURANONES IN VERY HIGH ENANTIOMERIC EXCESS, Tetrahedron letters, 37(13), 1996, pp. 2205-2208
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
13
Year of publication
1996
Pages
2205 - 2208
Database
ISI
SICI code
0040-4039(1996)37:13<2205:EGASO3>2.0.ZU;2-5
Abstract
The intermolecular asymmetric reduction of methyl o-(1-oxoalkyl)benzoa tes with B-chlorodiisopinocampheylborane provides, after workup, 3-alk ylphthalides in greater than or equal to 97% ee. Unfortunately, this p rocedure is not as efficient for the preparation of 3-arylphthalides. However, an intramolecular reduction of B-(o-benzoylbenzoyloxy)diisopi nocampheylborane readily prepared by the treatment of o-benzoyl benzoi c acid with diisopinocampheylborane, provides 3-phenylphthalide in gre ater than or equal to 96% ee.