Organocatalytic Asymmetric Mannich Reaction of 3‑Hydroxyoxindoles/3-Aminooxindoles with in Situ Generated N‑Boc-Protected Aldimines for the Synthesis of Vicinal Oxindole–Diamines/Amino Alcohols
A highly efficient asymmetric Mannich reaction of 3-monosubstituted 3-aminooxindoles/3-hydroxyoxindoles with in situ generated N-Boc-protected aldimines catalyzed by the chiral bifunctional thiourea–tertiary amine catalyst has been developed. Under mild reaction conditions, a series of structurally...
Saved in:
Published in | Journal of organic chemistry Vol. 81; no. 13; pp. 5270 - 5277 |
---|---|
Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
01.07.2016
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | A highly efficient asymmetric Mannich reaction of 3-monosubstituted 3-aminooxindoles/3-hydroxyoxindoles with in situ generated N-Boc-protected aldimines catalyzed by the chiral bifunctional thiourea–tertiary amine catalyst has been developed. Under mild reaction conditions, a series of structurally diverse vicinal oxindole–diamines/amino alcohols were smoothly obtained in moderate to high yields (up to 99%) with good to excellent diastereoselectivities and enantioselectivities (up to 95:5 dr and 96% ee). The synthetic application of this protocol was also demonstrated by the versatile transformation of chiral vicinal oxindole–diamine/amino alcohol into spirocyclic oxindoles. |
---|---|
Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.6b00278 |