Highly stereoselective prins cyclization of silylmethyl-substituted cyclopropyl carbinols to 2,4,6-trisubstituted tetrahydropyrans

被引：92

作者：

Yadav, VK ^{[1
]}

Kumar, NV ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 28期

关键词：

D O I：

10.1021/ja048000c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The homoallyl cation formed from a cyclopropyl carbinol that was vicinally substituted by a silylmethyl function underwent smooth Prins cyclization with aldehydes and ketones to form 2,4,6-trisubstituted tetrahydropyrans with very high stereoselectivity. Copyright © 2004 American Chemical Society.

引用

页码：8652 / 8653

页数：2

共 32 条

[1] Stereocontrolled synthesis of 2,4,5-trisubstituted tetrahydropyrans [J].

Al-Mutairi, EH ;

Crosby, SR ;

Darzi, J ;

Harding, JR ;

Hughes, RA ;

King, CD ;

Simpson, TJ ;

Smith, RW ;

Willis, CL .

CHEMICAL COMMUNICATIONS, 2001, (09) :835-836

[2] Aromatic 4-tetrahydropyranyl and 4-quinuclidinyl cations. Linking prins with Cope and Grob [J].

Alder, RW ;

Harvey, JN ;

Oakley, MT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :4960-4961

[3] Stereoselective synthesis of tetrahydropyrans via a formal [4+2]-cycloaddition of allylsilanes [J].

Angle, SR ;

El-Said, NA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10211-10212

[4]

[Anonymous], COMPREHENSIVE ORGANI

[5] The "Aqueous" prins reaction [J].

Aubele, DL ;

Lee, CA ;

Floreancig, PE .

ORGANIC LETTERS, 2003, 5 (23) :4521-4523

[6] Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans [J].

Barry, CSJ ;

Crosby, SR ;

Harding, JR ;

Hughes, RA ;

King, CD ;

Parker, GD ;

Willis, CL .

ORGANIC LETTERS, 2003, 5 (14) :2429-2432

[7] ACID-PROMOTED REACTION OF CYCLIC ALLYLIC DIOLS WITH CARBONYL-COMPOUNDS - STEREOSELECTIVE RING-ENLARGING TETRAHYDROFURAN ANNULATIONS [J].

BROWN, MJ ;

HARRISON, T ;

HERRINTON, PM ;

HOPKINS, MH ;

HUTCHINSON, KD ;

MISHRA, P ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5365-5378

[8] Synthesis of novel 2,6-disubstituted-3,4-dimethylidene tetrahydropyrans via Prins-type cyclization [J].

Cho, YS ;

Karupaiyan, K ;

Kang, HJ ;

Pae, AN ;

Cha, JH ;

Koh, HY .

CHEMICAL COMMUNICATIONS, 2003, (18) :2346-2347

[9] Stereocontrolled synthesis of trisubstituted tetrahydropyrans [J].

Cloninger, MJ ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :1092-1093

[10]

Fleming I., 1976, FRONTIER ORBITALS OR, P81

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