Unusual N-acylation of sterically congested trans-4,5-disubstituted 2-imidazolidinones:: remarkably facile C-C bond formation

被引：13

作者：

Abdel-Aziz, AAM ^{[1
]}

Matsunaga, H ^{[1
]}

Kunieda, T ^{[1
]}

机构：

[1] Kumamoto Univ, Fac Pharmaceut Sci, Kumamoto 8620973, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 37期

关键词：

D O I：

10.1016/S0040-4039(01)01348-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sterically congested trans-4,5-di-tert-butyl-2-imidazolidinone (DTBIm) and trans-4,5-di-(I-adamantyl)-2-imidazolidinone (DAIm), which are prepared from the parent 1,3-dihydro-2-imidazolone, undergo an unusual N-acylation reaction with acyl chlorides in the presence of organic amines to give the 3-oxoacyl derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6565 / 6567

页数：3

共 12 条

[1] An unusual enhancement of chiral induction by chiral 2-imidazolidinone auxiliaries [J].

Abdel-Aziz, AAM ;

Okuno, J ;

Tanaka, S ;

Ishizuka, T ;

Matsunaga, H ;

Kunieda, T .

TETRAHEDRON LETTERS, 2000, 41 (44) :8533-8537

[2] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[3]

Ager DJ, 1997, ALDRICHIM ACTA, V30, P3

[4]

[Anonymous], [No title captured]

[5] HIGHLY EFFICIENT CHIRAL 2-OXAZOLIDINONE AUXILIARIES DERIVED FROM METHYLCYCLOPENTADIENES AND 2-OXAZOLONE [J].

HASHIMOTO, N ;

ISHIZUKA, T ;

KUNIEDA, T .

TETRAHEDRON LETTERS, 1994, 35 (05) :721-724

[6] EXTREMELY POWERFUL CHIRAL AUXILIARIES - ENANTIOMERIC [4+2] CYCLOADDUCTS OF 2-OXAZOLONE AND 9,10-DIMETHYLANTHRACENE [J].

KIMURA, K ;

MURATA, K ;

OTSUKA, K ;

ISHIZUKA, T ;

HARATAKE, M ;

KUNIEDA, T .

TETRAHEDRON LETTERS, 1992, 33 (31) :4461-4464

[7] CONFORMATIONALLY RIGID CHIRAL [4+2]CYCLOADDUCT-BASED 2-OXAZOLIDINONES AS NEW AUXILIARIES [J].

MATSUNAGA, H ;

KIMURA, K ;

ISHIZUKA, T ;

HARATAKE, M ;

KUNIEDA, T .

TETRAHEDRON LETTERS, 1991, 32 (52) :7715-7718

[8] Stereoselective alkylations in rigid systems.: Effect of remote substituents on π-facial additions to lactam enolates.: Stereoelectronic and steric effects [J].

Meyers, AI ;

Seefeld, MA ;

Lefker, BA ;

Blake, JF ;

Williard, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7429-7438

[9] A new route to the synthesis of pyrazole and pyrimidine C-nucleoside derivatives [J].

Morelli, CF ;

Manferdini, M ;

Veronese, AC .

TETRAHEDRON, 1999, 55 (35) :10803-10814

[10]

Roos GHP, 1998, S AFR J CHEM-S-AFR T, V51, P7

← 1 2 →