Tetrahedron Letters p. 175 - 178 (1991)
Update date:2022-08-02
Topics:
Deng, Li
Czerwinski, Kevin
Cook, James M.
The Pictet-Spengler reaction of Nb-benzyl tryptophan methyl ester 4 with 5 in refluxing benzene yielded a mixture of cis and trans tetrahydro β-carbolines in a ratio of 7a(23)/7b(77), whereas the analogous reaction of isopropyl ester 10 with 5 provided increased trans stereoselectivity [cis(13):trans(87)]. The implications in regard to the role of intermediates 1-3 in this condensation are described. Moreover, Pictet-Spengler reaction of 4 or 10 with aldehydes (Ph, Δ) led to kinetic trapping of the cis/trans diastereomers, whereas reaction in TFA/CH2Cl2(25°C) provided tetrahydro β-carbolines via thermodynamic control and increased trans diastereoselectivity in most cases.
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