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Cation-controlled enantioselective and diastereoselective synthesis of indolines: an autoinductive phase-transfer initiated 5-endo-trig process

Abstract:

A catalytic enantioselective approach to the synthesis of indolines bearing two asymmetric centers, one of which is all-carbon and quaternary, is described. This reaction proceeds with high levels of diastereoselectivity (>20:1) and high levels of enantioselectivity (up to 99.5:0.5 er) in the presence of CsOH·H2O and a quinine-derived ammonium salt. The reaction most likely proceeds via a delocalized 2-aza-pentadienyl anion that cyclizes either by a suprafacial electrocyclic mechanism, o...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/jacs.5b08834

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Publisher:
American Chemical Society Publisher's website
Publication date:
2015-10-01
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
Source identifiers:
573186
Language:
eng
Pubs id:
pubs:573186
UUID:
uuid:842a5d0b-e644-4805-ba0c-68a1f5006a23
Local pid:
pubs:573186
Deposit date:
2016-02-03

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