Direct Trapping of Sterically Encumbered Aluminum Enolates

被引：25

作者：

Bleschke, Christian ^{[1
]}

Tissot, Matthieu ^{[1
]}

Mueller, Daniel ^{[1
]}

Alexakis, Alexandre ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 09期

基金：

瑞士国家科学基金会; 新加坡国家研究基金会;

关键词：

ASYMMETRIC CONJUGATE ADDITION; ENANTIOMERICALLY ENRICHED ZINC; GRIGNARD-REAGENTS; TRISUBSTITUTED ENONES; TANDEM; 1,4-ADDITION; CONSTRUCTION; CENTERS; AMINES;

D O I：

10.1021/ol400642y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The formation of chiral and sterically congested cyclohexanone derivatives has been achieved through a multistep sequence with one single purification step. (n-Butoxymethyl)-diethylamine was identified as a highly efficient reagent for the direct trapping of aluminum enolates. The Lewis acidic character of aluminum suffices to activate the alpha-aminoether to form in situ an electrophilic iminium species. In return the aluminum enolate is rendered more nucleophilic by coordination of the butoxy group and formation of an aluminate.

引用

页码：2152 / 2155

页数：4

共 40 条

[1] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].

Alexakis, A. ;

Backvall, J. E. ;

Krause, N. ;

Pamies, O. ;

Dieguez, M. .

CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823

[2] Highly enantioselective copper(I)-phosphoramidite-catalysed additions of organoaluminium reagents to enones [J].

Alexakis, A ;

Albrow, V ;

Biswas, K ;

d'Augustin, M ;

Prieto, O ;

Woodward, S .

CHEMICAL COMMUNICATIONS, 2005, (22) :2843-2845

[3] Tandem enantioselective conjugate addition-cyclopropanation. Application to natural products synthesis [J].

Alexakis, A ;

March, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8753-8757

[4]

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

[5] Enantioselective One-Pot Conjugate Addition of Grignard Reagents to Cyclic Enones Followed by Amidomethylation [J].

Bilcik, Filip ;

Drusan, Michal ;

Marak, Jozef ;

Sebesta, Radovan .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01) :760-765

[6] Enantioselective total synthesis of clavirolide C. applications of Cu-catalyzed asymmetric conjugate additions and Ru-catalyzed ring-closing metathesis [J].

Brown, M. Kevin ;

Hoveyda, Amir H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (39) :12904-+

[7] Tandem and domino catalytic strategies for enantioselective synthesis [J].

Chapman, Christopher J. ;

Frost, Christopher G. .

SYNTHESIS-STUTTGART, 2007, (01) :1-21

[8] Recent advances in metal-catalyzed asymmetric conjugate additions [J].

Christoffers, Jens ;

Koripelly, Girish ;

Rosiak, Anna ;

Roessle, Michael .

SYNTHESIS-STUTTGART, 2007, (09) :1279-1300

[9] Modular peptide-based phosphine ligands-in asymmetric catalysis: Efficient and enantioselective Cu-catalyzed conjugate additions to five-, six-, and seven-membered cyclic enones [J].

Degrado, SJ ;

Mizutani, H ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :755-756

[10] SYNTHESIS OF CYCLIC ACETYLENIC MANNICH-BASES [J].

EPSZTEIN, R ;

LEGOFF, N .

TETRAHEDRON LETTERS, 1985, 26 (27) :3203-3206

← 1 2 3 4 →