Catalyst-Dependent Stereodivergent and Regioselective Synthesis of Indole-Fused Heterocycles through Formal Cycloadditions of Indolyl-Allenes

• DOI: 10.1021/jacs.5b02080
• Publication Date: 2015-06-06T00:07:49Z
• Authors: Liang-Yong Mei; Yin Wei; Xiang-Ying Tang; Min Shi
• Keywords: Stereocenter; Allene; Synthon

Stereo- and regioselective construction of poly-heterocycles, especially those with several contiguous stereocenters, is still a challenge. In this paper, catalyst-dependent stereodivergent synthesis indole-fused heterocycles through formal cycloadditions indolyl-allenes has been developed. The reaction features total reversion an all-carbon quaternary stereocenter when gold or platinum complex was employed as the catalyst [3 + 2] cycloaddition allene indole, affording different diazabenzo[a]cyclopenta[cd]azulenes epimers, respectively. addition, in presence IPrAuCl AgNTf2, highly exo-type [2 observed, which served 2C synthon. This methodology provides simple straightforward approach for tricyclic systems under mild conditions atom-economical way.