Citation: Ye WANG, Zhan Zhu LIU, Shi Zhi CHEN, Xiao Tian LIANG. Asymmetric Pictet-Spengler Reactions: Synthesis of Tetrahydroisoquinoline Derivatives from L-DOPA[J]. Chinese Chemical Letters, ;2004, 15(5): 505-507. shu

Asymmetric Pictet-Spengler Reactions: Synthesis of Tetrahydroisoquinoline Derivatives from L-DOPA

Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050

Received Date: 17 April 2003

Fund Project: The author thanks the National Natural Science Foundation of China (Project No.:30371681) and Beijing Municipal Natural Science Foundation (Project No.:7042041) for the financial support.

The cis-1-substituted-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid esters 3 can be obtained in a highly diastereoselective fashion through 1,3-induction Pictet-Spengler (P-S) cyclization of the L-DOPA (3,4-dihydroxyphenylalanine) methyl ester with aromatic or aliphatic aldehydes under acidic conditions. Their epimers 4 are also obtained as minor products.
- Asymmetric synthesis,
- Pictet-Spengler reaction,
- tetrahydroisoquinoline,
- 1,3-induction,
- L-DOPA
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