Zinc-Mediated Diastereoselective Synthesis of 3-Amino Oxindoles by Addition of Methyl and Terminal Alkynes to N-tert-Butanesulfinyl Ketimines

• Published in: Journal of organic chemistry Vol. 77; no. 7; pp. 3311 - 3317
• Main Authors: Yan, Wenjin, Wang, Dong, Feng, Jingchao, Li, Peng, Wang, Rui
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.04.2012; Amer Chemical Soc
• Subjects: Alkynes - chemistry; Amines - chemistry; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Imines - chemistry; Indoles - chemical synthesis; Indoles - chemistry; Molecular Structure; Nitriles - chemistry; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; Sulfhydryl Compounds - chemistry; Zinc - chemistry; SULFINIMINES; HIGHLY ENANTIOSELECTIVE SYNTHESIS; AG-041R; ORGANOCATALYTIC ALPHA-AMINATION; ALDOL REACTION; IMINES; FACILE; CATALYTIC ASYMMETRIC-SYNTHESIS; DERIVATIVES; RECEPTOR ANTAGONIST; Protecting group; Acetylenic compound; Mild operating conditions; Nitrogen heterocycle; Lactam; Transition metal; Chiral compound; Diastereoselectivity; Zinc; Amine; Ketimine; Sulfoxide; Cleavage; Indole derivatives; Chemical synthesis; Alkyne
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo300110a

A zinc-mediated addition of methyl and terminal alkynes to chiral N-tert-butanesulfinyl ketimines for the preparation of optical quaternary 3-amino oxindoles was reported. In general, the operationally simple reaction affords the desired products in high yields and good to excellent diastereoselectivities. Subsequent convenient cleavage of sulfinyl protecting group under mild conditions was presented without racemization.