In:
Chemistry – A European Journal, Wiley, Vol. 20, No. 35 ( 2014-08-25), p. 11091-11100
Kurzfassung:
This article is a full account of the work exploring the potential utility of catalytic enantioselective amide allylation of various isatins using indium‐based chiral catalysts. A survey of various isatin substrates and NH‐containing stannylated reagents revealed that the reaction has a remarkably wide scope to result in extremely high yields and enantioselectivities (up to 〉 99 %, 99 % ee ) of variously substituted homoallylic alcohols. Several mechanistic investigations demonstrated that the substrate–reagent hydrogen‐bond interaction plays a critical role in the formation of the key transition states to result in enhanced catalytic reaction. The success of this approach allowed convenient access to chiral 2‐oxindoles spiro‐fused to the α‐methylene‐γ‐butyrolactone functionality and their halogenated derivatives in almost enantiopure forms, thus highlighting the general utility of this synthetic method to deliver a large variety of antineoplastic drug candidates and pharmaceutically meaningful compounds.
Materialart:
Online-Ressource
ISSN:
0947-6539
,
1521-3765
DOI:
10.1002/chem.201403357
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2014
ZDB Id:
1478547-X
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