Asymmetric conjugate addition of alkynylboronates to enones: Rationale for the intriguing catalysis exerted by binaphthols

Journal of the American Chemical Society

Volumn 128, Issue 10, 2006, Pages 3116-3117

  Pellegrinet, Silvina C ^a   Goodman, Jonathan M ^b  

^a Universidad Nacional de Rosario   (Argentina)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3,3' DIIODO 2,2' BIPHENOL; ALKYNYL GROUP; BORONIC ACID DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ATOM; CALCULATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOMER; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33644961540     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056727a     Document Type: Article

References (16)

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2. For the stoichiometric version of this reaction, see: Chong, J. M.; Shen, L.; Taylor N. J. J. Am. Chem. Soc. 2000, 122, 1822-1823.
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5. For a review on boron-substituted building blocks in cycloaddition reactions, see: Hilt, G.; Bolze. P. Synthesis 2005, 2091-2115.
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13. Silva, M. A.; Goodman, J. M. Tetrahedron Lett. 2003, 44, 8233-8236.
14. The hetero-Diels-Alder reaction shown in Scheme 2 could also generate the regioisomeric cycloadduct where the carbon bonded to boron in the alkynylboronate becomes attached to the β-carbon of the enone. However, we have not considered this possibility because the formation of this product should be less favored than the one shown due to electronic effects.
15. (a) Silva, M. A.; Pellegrinet, S. C.; Goodman, J. M. J. Org. Chem. 2002, 67, 8203-8209.
16. (b) Silva, M. A.; Pellegrinet, S. C.; Goodman, J. M. J. Org. Chem. 2003, 68, 4059-4066.