Chiral phosphoric acid-governed anti-diastereoselective and enantioselective Hetero-Diels - Alder reaction of glyoxylate

Journal of the American Chemical Society

Volumn 131, Issue 36, 2009, Pages 12882-12883

  Momiyama, Norie ^a   Tabuse, Hideaki ^a   Terada, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BINAPHTHYL; CHEMICAL EQUATIONS; CHIRAL LEWIS ACID; DIASTEREOSELECTIVE; DIASTEREOSELECTIVITIES; ENANTIOSELECTIVE; GLYOXYLATE; HETERO-DIELS-ALDER REACTIONS; PHENYL GROUP;

ACIDS; PHOSPHORIC ACID; STEREOSELECTIVITY;

CHEMICAL REACTIONS;

ALDEHYDE; ALKADIENE; BINAPHTHOL DERIVATIVE; CARBONYL DERIVATIVE; DIHYDROPYRAN; FUNCTIONAL GROUP; GLYOXYLIC ACID; HETEROCYCLIC COMPOUND; LEWIS ACID; METHOXYDIENE DERIVATIVE; NAPHTHOL DERIVATIVE; PHOSPHORIC ACID; PYRAN DERIVATIVE; SILOXYDIENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 70349083415     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904749x     Document Type: Article

References (20)

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17. 1H NMR spectrum of the crude product from the reaction of 3aa with 2 catalyzed by 1a revealed the exclusive presence of cycloadduct 4aa without the production of a Mukaiyama aldol adduct intermediate during the course of the reaction.
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19. The two-hydrogen-bond model of the TS structure has been proposed on the basis of our previous report (see ref 6c).
20. The manuscript is in preparation.