Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones

被引：71

作者：

Jing, Zhenzhong ^{[1
]}

Bai, Xiangbin ^{[1
]}

Chen, Wenchao ^{[1
]}

Zhang, Gao ^{[1
]}

Zhu, Bo ^{[1
]}

Jiang, Zhiyong ^{[1
]}

机构：

[1] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Jinming Campus, Kaifeng 475004, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 02期

关键词：

ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID; CATALYTIC ASYMMETRIC ADDITION; FRIEDEL-CRAFTS REACTIONS; HYDROXY PHOSPHONATES; BIFUNCTIONAL ORGANOCATALYSTS; CASCADE REACTION; BASE CATALYSIS; ESTERS; DERIVATIVES; ALKYLATION;

D O I：

10.1021/acs.orglett.5b03412

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic asymmetric vinylogous aldol reaction of activated allyls to activated acyclic ketones is disclosed. A variety of activated acyclic ketones, such as trifluoromethyl ketones, alpha-ketoesters, and alpha-keto phosphonates, were found to be involved forming diverse gamma-selective aldol adducts with high enantioselectivities (up to >99% ee). The method provides an effective, general strategy to access valuable chiral electron-withdrawing group-substituted tertiary hydroxyl-based carboxylic acids.

引用

页码：260 / 263

页数：4

共 74 条

[1] ACTIVE-SITE INHIBITORS OF ACETOLACTATE SYNTHASE [J].

ABELL, LM ;

HANNA, WS ;

KUNITSKY, KJ ;

KERSCHEN, JA .

PESTICIDE SCIENCE, 1995, 44 (01) :89-92

[2] Green Synthesis and Antioxidant Activity of Novel γ-Cyano-α-hydroxyphosphonate Derivatives [J].

Aouani, Iyadh ;

Lahbib, Karima ;

Touil, Soufiane .

MEDICINAL CHEMISTRY, 2015, 11 (02) :206-213

[3] Asymmetric Propargylation of Ketones Using Allenylboronates Catalyzed by Chiral Biphenols [J].

Barnett, David S. ;

Schaus, Scott E. .

ORGANIC LETTERS, 2011, 13 (15) :4020-4023

[4] Organocatalytic Asymmetric Vinylogous Aldol Reactions [J].

Bisai, Vishnumaya .

SYNTHESIS-STUTTGART, 2012, 44 (10) :1453-1463

[5] Comparative molecular field analysis and synthetic validation of a hydroxyamide-propofol binding and functional block of neuronal voltage-dependent sodium channels [J].

Brown, Milton L. ;

Eidam, Hilary A. ;

Paige, Mikell ;

Jones, Paulianda J. ;

Patel, Manoj K. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (19) :7056-7063

[6] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF 1-ACYL-4-((2-METHYL-3-PYRIDYL)CYANOMETHYL)PIPERAZINES AS PAF ANTAGONISTS [J].

CARCELLER, E ;

MERLOS, M ;

GIRAL, M ;

ALMANSA, C ;

BARTROLI, J ;

GARCIARAFANELL, J ;

FORN, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (20) :2984-2997

[7] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].

Casiraghi, G ;

Zanardi, F ;

Appendino, G ;

Rassu, G .

CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972

[8] The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress [J].

Casiraghi, Giovanni ;

Battistini, Lucia ;

Curti, Claudio ;

Rassu, Gloria ;

Zanardi, Franca .

CHEMICAL REVIEWS, 2011, 111 (05) :3076-3154

[9] Direct Catalytic Enantioselective Vinylogous Aldol Reaction of α-Branched Enals with Isatins [J].

Cassani, Carlo ;

Melchiorre, Paolo .

ORGANIC LETTERS, 2012, 14 (21) :5590-5593

[10] Structural elucidation of in vivo and in vitro metabolites of anisodine by liquid chromatography-tandem mass spectrometry [J].

Chen, Huaixia ;

Chen, Yong ;

Du, Peng ;

Han, Fengmei .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2007, 44 (03) :773-778

← 1 2 3 4 5 6 7 8 →