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Synfacts 2010(7): 0756-0756  
DOI: 10.1055/s-0029-1220136
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Synthesis of Chiral 3-Substituted Phthalides

Contributor(s): Victor Snieckus, Timothy Hurst
C.-H. Xing, Y.-X. Liao, P. He, Q.-S. Hu*
The City University of New York, Staten Island, USA
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

The synthesis of phthalides 3 via the addition of arylboronic acids 2 to methyl 2-formylbenzoate 1 and lactonization is reported. Three sets of conditions were identified under ­palladium, platinum, and rhodium catalysis. EDG, EWG, and ortho substituents were all equally well tolerated on the boronic acid, although no electron-poor examples were reported. A rhodium(I)-catalyzed asymmetric version of the reaction using SPINOL ligand 7 was also reported to give chiral phthalides 4, although the enantio­induction was only moderate.