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Beilstein J Org Chem. 2013 Aug 1;9:1559-64. doi: 10.3762/bjoc.9.177. eCollection 2013.

Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-b]indole derivatives.

Author information

  • 1Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.

Abstract

A chiral phosphoric acid-catalyzed selenofunctionalization of tryptamine derivatives provides access to 3a-(phenylselenyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole derivatives in high yields and with synthetically useful levels of enantioselectivity (up to 89% ee).

KEYWORDS:

catalysis; chiral phosphoric acid; hexahydropyrrolo[2,3-b]indole; indole alkaloids; natural products; selenofunctionalization

PMID:
23946855
PMCID:
PMC3740605
DOI:
10.3762/bjoc.9.177
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