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Pictet-Spengler condensation of N-sulfonyl-β-phenethylamines with α-chloro-α-phenylselenoesters. New synthesis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylates

✍ Scribed by Claudio C. Silveira; Carmem R. Bernardi; Antonio L. Braga; Teodoro S. Kaufman

Book ID: 104261741
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 263 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00958-2

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✦ Synopsis

The reaction of N-suifonyl-~-phenethylamines with a-chloro-a-phenylseleno acetate/propionate esters under Lewis acid promotion gives moderate to good yields of the corresponding 1,2,3,4-tetrahydroisoquinoline-lcarboxylates. Varying degrees of diastereoselection were obtained using chiral sulfonamides and~or esters. Employing this strategy, the achievement of a new total synthesis of Calycotomine is reported.

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