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Chiral Bicyclic Guanidine-Catalyzed Enantioselective Reactions of Anthrones

2006; American Chemical Society; Volume: 128; Issue: 42 Linguagem: Inglês

10.1021/ja064636n

1943-2984

Juan Shen, Thanh-Truc Nguyen, Yong‐Peng Goh, Weiping Ye, Xiao Fu, Junye Xu, Choon‐Hong Tan,

Molecular spectroscopy and chirality

Chiral bicyclic guanidine 1 was found to be an excellent catalyst for reactions between anthrones and various dienophiles. The catalyst can tolerate a range of substituents and substitution patterns, making several anthrone derivatives suitable for this reaction. Both Diels-Alder and Michael adducts were obtained in excellent yields, high regioselectivities, and high enantioselectivities. This is the first case of a highly enantioselective base-catalyzed anthrone Diels-Alder reaction.