A Versatile Synthesis of Unsymmetrical 3,3′-Bioxindoles: Stereoselective Mukaiyama Aldol Reactions of 2-Siloxyindoles with Isatins

A new synthesis of 3,3′-bioxindoles is reported that is well suited for the preparation of unsymmetrical structures. In the key step, 3-hydroxy-3,3′-bioxindoles are constructed by Mukaiyama aldol reaction of 2-siloxyindoles with isatins. These tertiary carbinols are formed in high diastereoselectivi...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2008-11, Vol.73 (22), p.9151-9154
Main Authors: Ellis, J. Michael, Overman, Larry E, Tanner, Huw R, Wang, Jocelyn
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Indoles - chemical synthesis
Indoles - chemistry
Isatin - chemistry
Ketones - chemistry
Organic chemistry
Organosilicon Compounds - chemistry
Preparations and properties
Stereoisomerism
Substrate Specificity
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A new synthesis of 3,3′-bioxindoles is reported that is well suited for the preparation of unsymmetrical structures. In the key step, 3-hydroxy-3,3′-bioxindoles are constructed by Mukaiyama aldol reaction of 2-siloxyindoles with isatins. These tertiary carbinols are formed in high diastereoselectivities, with substitution at various positions of the isatin and the 2-siloxyindole being tolerated.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801867w