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

被引：209

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 [J].

Aleman, Jose ;

Cabrera, Silvia ;

Maerten, Eddy ;

Overgaard, Jacob ;

Jorgensen, Karl Anker .

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 [J].

Armstrong, Alan ;

Convine, Nicola J. ;

Popkin, Matthew E. .

SYNLETT, 2006, (10) :1589-1591

[4] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].

Ballini, R ;

Bosica, G ;

Fiorini, D ;

Palmieri, A ;

Petrini, M .

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 [J].

Bertelsen, Slren ;

Marigo, Mauro ;

Brandes, Sebastian ;

Diner, Peter ;

Jorgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12973-12980

[7] Asymmetric organocatalytic β-hydroxylation of α,β-unsaturated aldehydes [J].

Bertelsen, Soren ;

Diner, Peter ;

Johansen, Rasmus Lyng ;

Jorgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) :1536-+

[8] Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions [J].

Brandau, Sven ;

Maerten, Eddy ;

Jorgensen, Karl Anker .

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 [J].

Brandau, Sven ;

Landa, Aitor ;

Franzen, Johan ;

Marigo, Mauro ;

Jorgensen, Karl Anker .

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 [J].

Camps, P ;

Muñoz-Torrero, D ;

Sánchez, L .

TETRAHEDRON-ASYMMETRY, 2004, 15 (13) :2039-2044

← 1 2 3 4 5 6 7 8 →