Enantioselective direct aldol-type reaction of azlactone via protonation of vinyl ethers by a chiral brønsted acid catalyst

Journal of the American Chemical Society

Volumn 131, Issue 10, 2009, Pages 3430-3431

  Terada, Masahiro ^a   Tanaka, Hiroyasu ^a   Sorimachi, Keiichi ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CATALYST; AMINO ACID DERIVATIVES; AZLACTONES; CARBON ATOMS; DIASTEREOSELECTIVE; ENANTIO; ENANTIOSELECTIVE; OXOCARBENIUM; STEREOGENIC CENTERS; VINYL ETHERS;

AMINES; AMINO ACIDS; CATALYSIS; CATALYSTS; ORGANIC ACIDS; PHOSPHORIC ACID; PROTONATION;

ETHERS;

ACID; AMINO ACID; AZLACTONE; CARBENOID; CARBON; CHIRAL BRONSTED ACID; ETHER DERIVATIVE; HYDROGEN; LACTONE DERIVATIVE; PHOSPHORIC ACID; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYST; CHEMICAL BOND; ENANTIOSELECTIVITY; PROTON TRANSPORT; STEREOCHEMISTRY; TEMPERATURE;

EID: 67749118135     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8090643     Document Type: Article

References (40)

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37. The high stereoselectivity observed would be attributed to the formation of contact ion pairs between the oxocarbenium ion (3) and conjugate base of the chiral phosphoric acid (2) through a C-H⋯O hydrogen bonding interaction, as illustrated in the plausible structures (A) of hydrogen bonding in Scheme 1. See Supporting Information for details.
38. 2 = Me), (Z)-1f (86% Z) and (E)-1f (97% E), exhibited identical diastereo- and enantioselectivities. See Supporting Information for details.
39. 2 = Me) did not provide any desired product, and it was recovered in > 80% yield.
40. The reaction of ortho-chloro substituted azlactone gave the corresponding product in <10% yield.