In:
Angewandte Chemie, Wiley, Vol. 131, No. 13 ( 2019-03-22), p. 4389-4393
Abstract:
A selectivity switch in a Rh II /carbene‐triggered cyclopentannulation with catalytic InCl 3 is reported for the first time, affording both diastereomers of the fused spiroindolines and an unusual bridged tetracyclic indoline in high yields with excellent selectivities. Mechanistic studies indicate an intramolecular annulation of the indole with an in situ formed aminocyclopropane. The stepwise thermal conversions from the kinetic spiroindoline to the metastable bridged indoline, and then to the thermodynamic spiroindoline, involving a ring‐opening rearrangement of a cyclopentane, is crucial for selectivity control.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v131.13
DOI:
10.1002/ange.201812294
Language:
English
Publisher:
Wiley
Publication Date:
2019
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514305-6
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505872-7
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1479266-7
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505867-3
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506259-7
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