Highly enantioselective direct alkylation of arylacetic acids with chiral lithium amides as traceless auxiliaries

Journal of the American Chemical Society

Volumn 133, Issue 31, 2011, Pages 11936-11939

  Stivala, Craig E ^a   Zakarian, Armen ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLACETIC ACIDS; CHIRAL AUXILIARIES; CHIRAL REAGENT; DIRECT ALKYLATION; ENANTIOSELECTIVE; ENANTIOSELECTIVE ALKYLATION; LITHIUM AMIDE;

AMIDES; LITHIUM;

ALKYLATION;

ACETIC ACID; AMIDE; CARBOXYLIC ACID; LITHIUM; LITHIUM AMIDE; PHENYLACETIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; REACTION OPTIMIZATION; STEREOCHEMISTRY;

ACETIC ACIDS; ALKYLATION; AMIDES; LITHIUM; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79961151891     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205107x     Document Type: Article

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46. We experimentally confirmed that the products are formed through enantioselective alkylation of the initially generated enediolate. Enolization of the product followed by a possible enantioselective protonation has been ruled out. See the Supporting Information (file Supporting Information 1, p S23) for details.
47. Preliminary studies revealed that under the standard conditions described herein, simple alkanoic acids (such as butyric acid) do not undergo highly enantioselective alkylation.