One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis

被引：47

作者：

Barber, David M. ^{[1
]}

Duris, Andrej ^{[1
]}

Thompson, Amber L. ^{[1
]}

Sanganee, Hitesh J. ^{[2
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] AstraZeneca R&D, Emerging Innovat, Alderley SK10 4GT, Cheshire, England

来源：

ACS CATALYSIS | 2014年 / 4卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

organocatalysis; gold catalysis; cascade reactions; nitro-Mannich; hydroamination; pyrrolidine; AZA-HENRY REACTION; ENANTIOSELECTIVE SYNTHESIS; BIFUNCTIONAL ORGANOCATALYSTS; INTRAMOLECULAR HYDROAMINATION; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION CASCADE; ABSOLUTE-STRUCTURE; MICHAEL ADDITION; ALLENES;

D O I：

10.1021/cs401008v

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The highly enantioselective preparation of trisubstituted pyrrolidinc derivatives employing a one-pot nitro-Mannich/hydroamination cascade is reported. This cascade approach utilizes an asymmetric bifunctional organo-catalytic nitro-Mannich reaction followed by a gold-catalyzed allene hydroamination reaction. The products are afforded in good yields and excellent diastereo- and enantioselectivities.

引用

页码：634 / 638

页数：5

共 74 条

[1] Asymmetric hydroamination of non-activated carbon-carbon multiple bonds [J].

Aillaud, Isabelle ;

Collin, Jacqueline ;

Hannedouche, Jerome ;

Schulz, Emmanuelle .

DALTON TRANSACTIONS, 2007, (44) :5105-5118

[2] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[3] Stereoselective Synthesis of Densely Functionalized Pyrrolidin-2-ones by a Conjugate Addition/Nitro-Mannich/Lactamization Reaction [J].

Anderson, James C. ;

Horsfall, Lisa R. ;

Kalogirou, Andreas S. ;

Mills, Matthew R. ;

Stepney, Gregory J. ;

Tizzard, Graham J. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (14) :6186-6198

[4] Enantioselective Conjugate Addition Nitro-Mannich Reactions: Solvent Controlled Synthesis of Acyclic anti- and syn-β-Nitroamines with Three Contiguous Stereocenters [J].

Anderson, James C. ;

Stepney, Gregory J. ;

Mills, Matthew R. ;

Horsfall, Lisa R. ;

Blake, Alexander J. ;

Lewis, William .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07) :1961-1971

[5] One-Pot Catalytic Enantioselective Synthesis of Tetrahydropyridines via a Nitro-Mannich/Hydroamination Cascade [J].

Barber, David M. ;

Sanganee, Hitesh J. ;

Dixon, Darren J. .

ORGANIC LETTERS, 2012, 14 (20) :5290-5293

[6] One-pot nitro-Mannich/hydroamination cascades for the direct synthesis of 2,5-disubstituted pyrroles using base and gold catalysis [J].

Barber, David M. ;

Sanganee, Hitesh ;

Dixon, Darren J. .

CHEMICAL COMMUNICATIONS, 2011, 47 (15) :4379-4381

[7] Telescoped Synthesis of Stereodefined Pyrrolidines [J].

Belmessieri, Dorine ;

Cordes, David B. ;

Slawin, Alexandra M. Z. ;

Smith, Andrew D. .

ORGANIC LETTERS, 2013, 15 (13) :3472-3475

[8] Enantioselective One-Pot Organocatalytic Michael Addition/Gold-Catalyzed Tandem Acetalization/Cyclization [J].

Belot, Sebastien ;

Vogt, Kim A. ;

Besnard, Celine ;

Krause, Norbert ;

Alexakis, Alexandre .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (47) :8923-8926

[9] CRYSTALS version 12: software for guided crystal structure analysis [J].

Betteridge, PW ;

Carruthers, JR ;

Cooper, RI ;

Prout, K ;

Watkin, DJ .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2003, 36 :1487-1487

[10] Gold(I)-Catalyzed Stereoconvergent, Intermolecular Enantioselective Hydroamination of Allenes [J].

Butler, Kristina L. ;

Tragni, Michele ;

Widenhoefer, Ross A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5175-5178

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