A versatile approach for the asymmetric synthesis of 3-alkyl-2,3-dihydro-1H-isoindolin-1-ones

被引：59

作者：

Chen, MD

Zhou, X

He, MZ

Ruan, YP

Huang, PQ ^{[1
]}

机构：

[1] Xiamen Univ, Dept Chem, Xiamen 361005, Fujian, Peoples R China

[2] Xiamen Univ, Key Lab Chem Biol Fujian Province, Xiamen 361005, Fujian, Peoples R China

来源：

TETRAHEDRON | 2004年 / 60卷 / 07期

基金：

高等学校博士学科点专项科研基金; 中国国家自然科学基金;

关键词：

isoindolin-1-one; chiral auxiliary; benzyloxyphenylglycinol; asymmetric synthesis;

D O I：

10.1016/j.tet.2003.11.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Based on the use of (R)-p-benzyloxyphenylglycinol (10) as a new oxidatively cleavable chiral auxiliary, a flexible approach to (R)-3-alkyl-2,3-dihydro-1H-isoindolin-1-ones via a diastereoselective reductive-alkylation is developed. The oxidative cleavage of the chiral auxiliary by CAN under mild conditions ensured the access to (R)-3-alkyl-2,3-dihydro-1H-isoindolin-1-ones with ee at least 92%. (C) 2003 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1651 / 1657

页数：7

相关论文

共 61 条

[1] Diastereoselective and regioselective singlet-oxygen ene reaction of oxazolidine-substituted alkenes: Control through hydrogen bonding mediated by the urea functionality of chiral auxiliaries [J].

Adam, W ;

Peters, K ;

Peters, EM ;

Schambony, SB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (31) :7610-7611

[2] Regio- and stereocontrolled formation of chiral epoxy oxazolidines via bromocarbamation of N-Boc alkenyl oxazolidines. Application to asymmetric synthesis [J].

Agami, C ;

Couty, F ;

Hamon, L ;

Venier, O .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2106-2112

[3] Selective N-dealkylation of tertiary amines derived from phenylglycinol or ephedrine family [J].

Agami, C ;

Couty, F ;

Evano, G .

TETRAHEDRON LETTERS, 1999, 40 (19) :3709-3712

[4] Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives [J].

Allin, SM ;

Northfield, CJ ;

Page, MI ;

Slawin, AMZ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (11) :1715-1721

[5] A NEW CHIRAL GLYCINE SYNTHON - SYNTHESIS, X-RAY STRUCTURE OF (-)BULLET(2S,4R)-2-ETHOXYCARBONYL-4-PHENYL-1,3-OXAZOLIDINE AND DIASTEREOSELECTIVE NUCLEOPHILIC RING-OPENING TO (R)-ETHYL ALPHA-AMINO CARBOXYLATES [J].

ANDRES, C ;

GONZALEZ, A ;

PEDROSA, R ;

PEREZENCABO, A ;

GARCIAGRANDA, S ;

SALVADO, MA ;

GOMEZBELTRAN, F .

TETRAHEDRON LETTERS, 1992, 33 (33) :4743-4746

[6] Isoindolinone enantiomers having affinity for the dopamine D4 receptor [J].

Belliotti, TR ;

Brink, WA ;

Kesten, SR ;

Rubin, JR ;

Wustrow, DJ ;

Zoski, KT ;

Whetzel, SZ ;

Corbin, AE ;

Pugsley, TA ;

Heffner, TG ;

Wise, LD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (12) :1499-1502

[7] Synthesis of enantiomerically pure α-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines [J].

Blanchet, J ;

Bonin, M ;

Micouin, L ;

Husson, HP .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6423-6426

[8]

BROMBERG O, 1896, CHEM BER, V29, P1434

[9] A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND 5-SUBSTITUTED PYRROLIDINONES [J].

BURGESS, LE ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1656-1662

[10] A simple and efficient synthetic route to chiral isopavines. Synthesis of (-)-O-methylthalisopavine and (-)-amurensinine [J].

Carrillo, L ;

Badia, D ;

Dominguez, E ;

Vicario, JL ;

Tellitu, I .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6716-6721

← 1 2 3 4 5 6 7 →