Tandem Transesterification and Diastereoselective Intramolecular Cycloaddition of α-Methoxycarbonylnitrones with Chiral Acyclic Allyl Alcohols

Osamu Tamura; Tatsuya Yamaguchi; Toshiyuki Okabe; Masanori Sakamoto

doi:10.1055/s-1994-22948

Synlett 1994; 1994(8): 620-622
DOI: 10.1055/s-1994-22948

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Tandem Transesterification and Diastereoselective Intramolecular Cycloaddition of α-Methoxycarbonylnitrones with Chiral Acyclic Allyl Alcohols

Osamu Tamura^* , Tatsuya Yamaguchi, Toshiyuki Okabe, Masanori Sakamoto

^*Meiji College of Pharmacy, Nozawa, Setagaya, Tokyo 154, Japan

Abstract

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Tandem transesterification and diastereoselective intramolecular 1,3-dipolar cycloaddition of α-methoxycarbonylnitrones (1a-d) with chiral acyclic secondary allyl alcohols [(Z)-2 and (E)-2)] are described. While reactions of 1a-d with (Z)-2 gave 3a-d with high stereoselectivities in excellent yields, 1d bearing (S)-1-phenylethyl group reacted with (E)-2 to give 6d with high selectivity.

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