3,3'-Br₂-BINOL-Zn Complex: A Highly Efficient Catalyst for the Enantioselective Hetero-Diels-Alder Reaction

Haifeng Du, Jiang Long, Jieyu Hu, Xin Li and Kuiling Ding*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, The People's Republic of China, Email: kdingpub.sioc.ac.cn

H. Du, J. Long, J. Hu, X. Li, K. Ding, Org. Lett., 2002, 4, 4349-4352.

DOI: 10.1021/ol027034r (free Supporting Information)

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Abstract

A BINOLate-zinc complex prepared in situ from Et₂Zn and 3,3'-dibromo-BINOL is an efficient catalyst for the enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes to give 2-substituted 2,3-dihydro-4H-pyran-4-ones in up to quantitative yield and 98% ee.

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Key Words

Diels-Alder Reaction, O-Heterocycles

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ID: J54-Y2002-340