Tetrahedron Letters p. 2205 - 2208 (1996)
Update date:2022-08-17
Topics:
Ramachandran, P. Veeraraghavan
Chen, Guang-Ming
Brown, Herbert C.
The intermolecular asymmetric reduction of methyl o-(1-oxoalkyl)benzoates with B-chlorodiisopinocampheylborane provides, after workup, 3-alkylphthalides in ≥ 97% ee. Unfortunately, this procedure is not as efficient for the preparation of 3-arylphthalides. However, an intramolecular reduction of B-(o-benzoylbenzoyloxy)diisopinocampheylborane, readily prepared by the treatment of o-benzoyl benzoic acid with diisopinocampheylborane, provides 3-phenylphthalide in ≥ 96% ee.
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