Highly stereloselective synthesis of 2,5-disubstituted 3-vinylidene tetetrahydrofurans via Prins-type cyclization

被引：40

作者：

Shin, C

Chavre, SN

Pae, AN

Cha, JH

Koh, HY

Chang, MH

Choi, JH

Cho, YS

机构：

[1] Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea

[2] Hanyang Univ, Dept Chem, Seoul 133791, South Korea

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 15期

关键词：

D O I：

10.1021/ol051058r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthetic methodology for 2,5-disubstituted tetrahydrofurans having an allenyl group at the 3-position via Prins-type cyclization was developed. The reaction led to excellent selectivity and moderate to high yields.

引用

页码：3283 / 3285

页数：3

共 39 条

[31] Synthesis of enantiomerically pure substituted tetrahydrofurans from epoxides and phenylselenium reagents [J].

Tiecco, M ;

Testaferri, L ;

Bagnoli, L ;

Purgatorio, V ;

Temperini, A ;

Marini, F ;

Santi, C .

TETRAHEDRON-ASYMMETRY, 2004, 15 (03) :405-412

[32] STEREOCONTROLLED SYNTHESIS OF TRANS-2,5-DISUBSTITUTED TETRAHYDROFURANS [J].

TING, PC ;

BARTLETT, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (09) :2668-2671

[33] A novel stereoselective cyclization to functionalized dihydropyrans [J].

Viswanathan, GS ;

Yang, J ;

Li, CJ .

ORGANIC LETTERS, 1999, 1 (07) :993-995

[34] FURANOSIDES AND FURANONES BEARING ACRYLATE SIDE-CHAINS VIA PALLADIUM-MEDIATED CYCLIZATIONS OF GAMMA-OXOALLENES [J].

WALKUP, RD ;

MOSHER, MD .

TETRAHEDRON, 1993, 49 (41) :9285-9294

[35] Stereoselective synthesis of tetrahydrofurans via the palladium-catalyzed reaction of aryl bromides with γ-hydroxy alkenes:: Evidence for an unusual intramolecular olefin insertion into a Pd(Ar)(OR) intermediate [J].

Wolfe, JP ;

Rossi, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1620-1621

[36] Highly stereoselective prins cyclization of silylmethyl-substituted cyclopropyl carbinols to 2,4,6-trisubstituted tetrahydropyrans [J].

Yadav, VK ;

Kumar, NV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8652-8653

[37] Highly effective synthesis of 4-halo-tetrahydropyrans via a highly diastereoselective in situ prins-type cyclization reaction [J].

Yang, J ;

Viswanathan, GS ;

Li, CJ .

TETRAHEDRON LETTERS, 1999, 40 (09) :1627-1630

[38] Diastereoselective synthesis of polysubstituted tetrahydropyrans and thiacyclohexanes via indium trichloride mediated cyclizations [J].

Yang, XF ;

Mague, JT ;

Li, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :739-747

[39] Diastereoselective synthesis of 2,4-disubstituted tetrahydropyranols and ethers via a Prins-type cyclization catalyzed by scandium triflate [J].

Zhang, WC ;

Li, CJ .

TETRAHEDRON, 2000, 56 (16) :2403-2411

← 1 2 3 4 →