Michael addition of chloroalkyloxazolines to electron-poor alkenes: Synthesis of heterosubstituted cyclopropanes

被引：20

作者：

Rocchetti, MT

Fino, V

Capriati, V

Florio, S

Luisi, R

机构：

[1] Univ Bari, Dipartimento Farmacochim, I-70125 Bari, Italy

[2] CNR, ICCOM, Sez Bari, I-70126 Bari, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 04期

关键词：

D O I：

10.1021/jo026661r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiated 2-(1-chloroethyl)-4,4-dimethyl-2-oxazoline 7 adds to electron-poor alkenyl heterocycles to afford substituted cyclopropanes in excellent yields. A route to chiral nonracemic heterosubstituted cyclopropanes, starting from optically active 2-chloromethyl-2-oxazolines, is highlighted as well.

引用

收藏

页码：1394 / 1400

页数：7

相关论文

共 33 条

[1] Diheteroarylmethanes .5. E-Z isomerism of carbanions substituted by 1,3-azoles: C-13 and N-15 pi-charge shift relationships as source for mapping charge and ranking the electron-withdrawing power of heterocycles [J].

Abbotto, A ;

Bradamante, S ;

Pagani, GA .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1761-1769

[2] CHARGE MAPPING IN CARBANIONS - WEAK CHARGE DEMAND OF THE CYANO GROUP AS ASSESSED FROM A C-13 NMR-STUDY OF CARBANIONS OF ALPHA-ACTIVATED ACETONITRILES AND PHENYLACETONITRILES - BREAKDOWN OF A MYTH [J].

ABBOTTO, A ;

BRADAMANTE, S ;

PAGANI, GA .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :449-455

[3] A NMR investigation of alpha-heterosubstituted chloroethyllithiums in THF [J].

Abbotto, A ;

Bradamante, S ;

Florio, S ;

Capriati, V .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8937-8940

[4] Mechanistic investigations on the reaction between 1,2-dioxines and bulky stabilized phosphorus ylides: An efficient route to closely related cyclopropane stereoisomers [J].

Avery, TD ;

Fallon, G ;

Greatrex, BW ;

Pyke, SM ;

Taylor, DK ;

Tiekink, ERT .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7955-7966

[5] A new route to diastereomerically pure cyclopropanes utilizing stabilized phosphorus ylides and γ-hydroxy enones derived from 1,2-dioxines:: Mechanistic investigations and scope of reaction [J].

Avery, TD ;

Taylor, DK ;

Tiekink, ERT .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5531-5546

[6] Total synthesis of the pentacyclopropane antifungal agent FR-900848 [J].

Barrett, AGM ;

Kasdorf, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (45) :11030-11037

[7] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463

[8] TRIPYRIDYLCYCLOPROPENE DERIVATIVES AND THEIR CONVERSION TO HEXAPYRIDYLBENZENE [J].

BRESLOW, R ;

CRISPINO, GA .

TETRAHEDRON LETTERS, 1991, 32 (05) :601-604

[9]

Capriati V, 2002, EUR J ORG CHEM, V2002, P2961, DOI 10.1002/1099-0690(200209)2002:17<2961::AID-EJOC2961>3.0.CO

[10]

2-F

← 1 2 3 4 →