Highly Diastereo- and Enantioselective CuH-Catalyzed Synthesis of 2,3-Disubstituted Indolines

Journal of the American Chemical Society

Volumn 137, Issue 14, 2015, Pages 4666-4669

  Ascic, Erhad ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; FUNCTIONAL GROUPS;

CATALYZED SYNTHESIS; ENANTIOSELECTIVE; FUNCTIONALIZED; HETEROCYCLES; HIGH YIELD; MILD REACTION CONDITIONS; SUBSTITUTED AROMATIC;

SYNTHESIS (CHEMICAL);

BENZOIC ACID; BENZONITRILE; BROMIDE; COPPER; INDOLE DERIVATIVE; PHENOL; TETRACHLOROETHANE; ALDEHYDE; INDOLINE; STYRENE;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; HYDROGENATION; PROTON TRANSPORT; REACTION OPTIMIZATION; SYNTHESIS; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; COPPER; INDOLES; STEREOISOMERISM; STYRENE;

EID: 84927930877     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b02316     Document Type: Article

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51. This technique could also be applied on crude imines directly after solvent evaporation, as exemplified on 1a, although the yield was somewhat lower (74% isolated yield, 90% ee). Unfortunately, no product was observed on aliphatic imines, as demonstrated on (E)-2-methyl-N-(2-vinylphenyl)propan-1-imine.
52. The absolute configuration of 2s was determined to be 2R,3S by X-ray analysis (see Table 2). Consequently, those of the other products were assigned by analogy.