Diphenylprolinol silyl ether as catalyst of an asymmetric, catalytic, and direct Michael reaction of nitroalkanes with α,β-unsaturated aldehydes

被引：207

作者：

Gotoh, Hiroaki ^{[1
]}

Ishikawa, Hayato ^{[1
]}

Hayashi, Yujilro ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 25期

关键词：

D O I：

10.1021/ol702545z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic enantioselective direct conjugate addition of nitroalkanes to alpha,beta-unsaturated aldehydes using diphenylprolinol silyl ether as an organocatalyst has been developed. Using this methodology as a key step, short syntheses of therapeutically useful compounds have also been accomplished.

引用

页码：5307 / 5309

页数：3

共 74 条

[1] Asymmetric organocatalytic α-arylation of aldehydes
Aleman, Jose
Cabrera, Silvia
Maerten, Eddy
Overgaard, Jacob
Jorgensen, Karl Anker
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) : 5520 - 5523
[2] [Anonymous], 2000, CATALYTIC ASYMMETRIC
[3] Diastereoselective conjugate addition of cyanide to α,β-unsaturated oxazolidinones:: Enantioselective synthesis of ent-pregabalin and baclofen
Armstrong, Alan
Convine, Nicola J.
Popkin, Matthew E.
[J]. SYNLETT, 2006, (10) : 1589 - 1591
[4] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results
Ballini, R
Bosica, G
Fiorini, D
Palmieri, A
Petrini, M
[J]. CHEMICAL REVIEWS, 2005, 105 (03) : 933 - 971
[5] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[6] Dienamine catalysis:: Organocatalytic asymmetric γ-amination of α,β unsaturated aldehydes
Bertelsen, Slren
Marigo, Mauro
Brandes, Sebastian
Diner, Peter
Jorgensen, Karl Anker
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12973 - 12980
[7] Asymmetric organocatalytic β-hydroxylation of α,β-unsaturated aldehydes
Bertelsen, Soren
Diner, Peter
Johansen, Rasmus Lyng
Jorgensen, Karl Anker
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) : 1536 - +
[8] Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions
Brandau, Sven
Maerten, Eddy
Jorgensen, Karl Anker
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) : 14986 - 14991
[9] Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones
Brandau, Sven
Landa, Aitor
Franzen, Johan
Marigo, Mauro
Jorgensen, Karl Anker
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4305 - 4309
[10] Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries
Camps, P
Muñoz-Torrero, D
Sánchez, L
[J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (13) : 2039 - 2044

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