Probing the mechanism of Prins cyclisations and application to the synthesis of 4-hydroxytetrahydropyrans

被引：60

作者：

Barry, CS

Bushby, N

Harding, JR

Hughes, RA

Parker, GD

Roe, R

Willis, CL

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] AstraZeneca UK Ltd, Macclesfield SK10 4TG, Cheshire, England

来源：

CHEMICAL COMMUNICATIONS | 2005年 / 29期

关键词：

D O I：

10.1039/b504562b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Trapping intermediates on the Prins cyclisation pathway with carbon-based nucleophiles has given further insight into factors affecting the acid-mediated reactions of homoallylic alcohols with aldehydes, enabling the design of efficient syntheses of 4-hydroxy-2,6-disubstituted tetrahydropyrans.

引用

收藏

页码：3727 / 3729

页数：3

相关论文

共 25 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]

[Anonymous], SPART

[4] 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

[5] B-ALLYLDIISOPINOCAMPHEYLBORANE - A REMARKABLE REAGENT FOR THE DIASTEREOSELECTIVE ALLYLBORATION OF ALPHA-SUBSTITUTED CHIRAL ALDEHYDES [J].

BROWN, HC ;

BHAT, KS ;

RANDAD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :319-320

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

Cloninger, MJ ;

Overman, LE .

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

[7] Prins cyclizations: Labeling studies and application to natural product synthesis [J].

Crosby, SR ;

Harding, JR ;

King, CD ;

Parker, GD ;

Willis, CL .

ORGANIC LETTERS, 2002, 4 (20) :3407-3410

[8] Oxonia-cope rearrangement and side-chain exchange in the prins cyclization [J].

Crosby, SR ;

Harding, JR ;

King, CD ;

Parker, GD ;

Willis, CL .

ORGANIC LETTERS, 2002, 4 (04) :577-580

[9] Oxonia-Cope Prins cyclizations: A facile method for the synthesis of tetrahydropyranones bearing quaternary centers [J].

Dalgard, JE ;

Rychnovsky, SD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (48) :15662-15663

[10] The synthesis of mono- and bicyclic ethers via acid catalysed ring-opening cyclisation of tetrahydropyranyl ether derivatives [J].

Dixon, DJ ;

Ley, SV ;

Tate, EW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12) :1829-1836