Asymmetric synthesis of β-aryl-β-trifluoromethyl-β-aminoarones via Mannich-type reactions of ketone enolates with chiral aryl CF3-substituted N-tert-butanesulfinyl ketimines

被引：24

作者：

Liu, Yingle ^{[1
]}

Huang, Yangen ^{[1
]}

Qing, Feng-Ling ^{[1
,2
]}

机构：

[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 25期

基金：

中国国家自然科学基金;

关键词：

Mannich addition; Aminoarone; N-tert-Butanesulfinyl ketimine; Trifluoromethyl; Asymmetric; ALPHA-DIFLUOROMETHYL AMINES; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE ADDITION; ORGANOMETALLIC REAGENTS; ALCOHOLS; OXIDATION;

D O I：

10.1016/j.tet.2012.04.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the preparation of chiral beta-aryl-beta-trifluoromethyl-beta-aminoarones has been developed involving the Mannich-type reactions of ketone-derivative enolates with chiral aryl CF3-substituted N-tert-butanesulfinyl ketimines. This method tolerates a wide of aromatic ketones, giving the products in moderate to excellent yields (up to 91%) with good diastereoselectiveties (up to 93:7 dr). Acidic cleavage of the tert-butanesulfinyl group gave optically pure beta-aryl-beta-trifluoromethyl-beta-aminoarones in excellent yields (up to 98%), which can be further transformed into CF3-substituted aziridine derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：4955 / 4961

页数：7

共 41 条

[1] INTRAMOLECULAR THERMAL CYCLIZATION REACTIONS OF DIACRYLOYLAMINES [J].

ALDER, A ;

BELLUS, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6712-6714

[2] Diastereoselective addition of chlorotitanium enolate of N-acyl thiazolidinethione to O-methyl oximes:: A novel, stereoselective synthesis of α,β-disubstituted β-amino carbonyl compounds via chiral auxiliary mediated azetine formation [J].

Ambhaikar, NB ;

Snyder, JP ;

Liotta, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3690-3691

[3]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[4]

2-E

[5]

Daniel M., 2006, TETRAHEDRON, V62, P8869

[6] Simple and Efficient Access to N-Tosyl β-Amino Ketones and Their Conversion into 2,4-Disubstituted Azetidines [J].

Das, Biswanath ;

Balasubramanyam, Penagaluri ;

Veeranjaneyulu, Boyapati ;

Reddy, Gandolla Chinna .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) :9505-9508

[7] Total synthesis of (5R,6R,8R,9S)-(-)-5,9Z-indolizidine 221T using sulfinimine-derived N-sulfinyl β-amino ketones [J].

Davis, Franklin A. ;

Song, Minsoo ;

Qiu, Hui ;

Chai, Jing .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (24) :5067-5073

[8] Asymmetric Synthesis of Substituted Tropinones Using the Intramolecular Mannich Cyclization Reaction and Acyclic N-Sulfinyl β-Amino Ketone Ketals [J].

Davis, Franklin A. ;

Theddu, Naresh ;

Gaspari, Paul M. .

ORGANIC LETTERS, 2009, 11 (07) :1647-1650

[9] Applications of tert-butanesulfinamide in the asymmetric synthesis of amines [J].

Ellman, JA .

PURE AND APPLIED CHEMISTRY, 2003, 75 (01) :39-46

[10] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines [J].

Ellman, JA ;

Owens, TD ;

Tang, TP .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) :984-995

← 1 2 3 4 5 →