Citation: Wen PEI, Eiji WADA, Shuji KANEMASA. Asymmetric Diels-Alder Reaction of 1-(S_R)-p-Tolylsulfinyl-3-penten-2-one with Cyclopentadiene Catalzed by a Chiral Titanium Reagent[J]. Chinese Chemical Letters, ;1997, 8(11): 935-936. shu

Asymmetric Diels-Alder Reaction of 1-(S_R)-p-Tolylsulfinyl-3-penten-2-one with Cyclopentadiene Catalzed by a Chiral Titanium Reagent

a Department of Chemistry, Yanbian University, Yanji, 133002;
b Institute of Advanced Material study, Kyushu University, Kasugakoen, Kasuga 816, Japan

Received Date: 9 July 1997

Double asymmetric Diels-Alder reaction of 1-(S_R)-p-Tolylsulfinyl-3-penten-2-one with cyclopentadiene using a chiral titanium reagent was performed.The diastereoselectivity dependent on the size of aryl substituent involved in the chiral ligands was discussed.Absolute configuration of the cycloadducts was confirmed.Dramatic reversal of selectivity is observed.
1. [1]
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16. [16]
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19. [19]
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20. [20]
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