CuH-catalyzed asymmetric conjugate reductions of acyclic enones

被引：133

作者：

Lipshutz, BH ^{[1
]}

Servesko, JM ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem, Santa Barbara, CA 93106 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 39期

关键词：

conjugate reductions; copper hydride; enones; hydrosilylation; phosphane ligands;

D O I：

10.1002/anie.200352313

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A powerful new reaction has been developed for the asymmetric 1, 4-reduction of prochiral enones (see scheme). The key ingredients in this exceedingly mild and straightforward procedure are catalytic quantities of CuH, a readily available nonracemic phosphane ligand such as that shown, and inexpensive polymethyl-hydrosiloxane (PMHS) as the stoichiometric source of hydride.

引用

页码：4789 / 4792

页数：4

共 49 条

[1] Asymmetric synthesis with N-heterocyclic carbenes.: Application to the copper-catalyzed conjugate addition [J].

Alexakis, A ;

Winn, CL ;

Guillen, F ;

Pytkowicz, J ;

Roland, S ;

Mangeney, P .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (03) :345-348

[2] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].

Alexakis, A ;

Benhaim, C ;

Rosse, S ;

Humam, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263

[3]

Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221

[4]

Amengual R, 2002, SYNLETT, P1791

[5]

[Anonymous], UNPUB

[6] Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine-copper catalyst [J].

Appella, DH ;

Moritani, Y ;

Shintani, R ;

Ferreira, EM ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9473-9474

[7] New class of chiral diphosphine ligands for highly efficient transition metal-catalyzed stereoselective reactions: The bis(diphenylphosphino) five-membered biheteroaryls [J].

Benincori, T ;

Brenna, E ;

Sannicolo, F ;

Trimarco, L ;

Antognazza, P ;

Cesarotti, E ;

Demartin, F ;

Pilati, T .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6244-6251

[8] Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones [J].

Bennett, SMW ;

Brown, SM ;

Cunningham, A ;

Dennis, MR ;

Muxworthy, JP ;

Oakley, MA ;

Woodward, S .

TETRAHEDRON, 2000, 56 (18) :2847-2855

[9] Solvias Josiphos ligands: from discovery to technical applications [J].

Blaser, HU ;

Brieden, W ;

Pugin, B ;

Spindler, F ;

Studer, M ;

Togni, A .

TOPICS IN CATALYSIS, 2002, 19 (01) :3-16

[10] Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis [J].

Boaz, NW ;

Debenham, SD ;

Mackenzie, EB ;

Large, SE .

ORGANIC LETTERS, 2002, 4 (14) :2421-2424

← 1 2 3 4 5 →