Electrophilic cyclizations of vinylcyclopropanols to tethered aldehydes

被引：36

作者：

Youn, JH ^{[1
]}

Lee, J ^{[1
]}

Cha, JK ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 18期

关键词：

D O I：

10.1021/ol016490x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The intramolecular, stereoselective addition of 1-vinylcyclopropanols to tethered aldehydes has been achieved under mild conditions. Thus, sequential application of the titanium-mediated cyclopropanation of alpha,beta -unsaturated esters and the electrophilic cyclization of the aldehyde-tethered cyclopropanol products provides the facile formation of carbocyclic rings.

引用

收藏

页码：2935 / 2938

页数：4

相关论文

共 37 条

[1]

[Anonymous], COMPREHENSIVE ORGANI

[2] Novel platinum-catalyzed ring-opening of 1,2-cyclopropanated sugars with alcohols. Stereoselective synthesis of 2-C-branched glycosides [J].

Beyer, J ;

Madsen, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (46) :12137-12138

[3]

BODDANOWICZ MJ, 1974, ORG SYNTH, V54, P27

[4] IRON(III) MEDIATED TRANSFORMATIONS OF CYCLOPROPYLTRIMETHYLSILYL ETHERS .1. FREE-RADICAL TANDEM RING EXPANSION-CYCLIZATION REACTIONS FOR THE RAPID CONSTRUCTION OF [N30] BICYCLIC RING-SYSTEMS [J].

BOOKERMILBURN, KI ;

THOMPSON, DF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (18) :2315-2321

[5]

Bronson J. J., 1991, COMPREHENSIVE ORGANI, V5, P999

[6] Intramolecular [3+2] annulation of olefin-tethered cyclopropylamines [J].

Ha, JD ;

Lee, JW ;

Blackstock, SC ;

Cha, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8510-8514

[7] THE SESTERTERPENOIDS [J].

HANSON, JR .

NATURAL PRODUCT REPORTS, 1992, 9 (05) :481-489

[8] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .10. "TRIMETHYLSILYLDIAZOMETHANE(TMSCHN2) - A NEW, STABLE, AND SAFE REAGENT FOR THE HOMOLOGATION OF KETONES [J].

HASHIMOTO, N ;

AOYAMA, T ;

SHIOIRI, T .

TETRAHEDRON LETTERS, 1980, 21 (48) :4619-4622

[9] Platinum(II)-catalyzed isomerization of alkoxycyclopropanes to alkylated ketones [J].

Hoberg, JO ;

Jennings, PW .

ORGANOMETALLICS, 1996, 15 (18) :3902-3904

[10] Formation of seven-membered oxacycles through ring expansion of cyclopropanated carbohydrates [J].

Hoberg, JO .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6615-6618

← 1 2 3 4 →