Highly effective synthesis of 4-halo-tetrahydropyrans via a highly diastereoselective in situ prins-type cyclization reaction

被引：102

作者：

Yang, J ^{[1
]}

Viswanathan, GS ^{[1
]}

Li, CJ ^{[1
]}

机构：

[1] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(99)00027-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of aldehyde with homoallyl alcohols mediated by indium trichloride generated 4-chlorotetrahydropyrans in high yields and,vith high stereoselectivity. The same type of compounds can be generated through a single step, multi-component coupling between aldehyde and allyl bromide mediated by indium (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1627 / 1630

页数：4

共 18 条

[1] ADAMS DR, 1977, SYNTHESIS-STUTTGART, P661
[2] THE OLEFIN ALDEHYDE CONDENSATION - THE PRINS REACTION
ARUNDALE, E
MIKESKA, LA
[J]. CHEMICAL REVIEWS, 1952, 51 (03) : 505 - 555
[3] Indium trichloride (InCl3)catalyzed imino Diels-Alder reactions:: An efficient synthesis of cyclopentaquinolines, azabicyclooctanones and azabicyclononanones.
Babu, G
Perumal, PT
[J]. TETRAHEDRON, 1998, 54 (08) : 1627 - 1638
[4] CINTAS P, 1995, SYNLETT, P1087
[5] COPPI L, 1988, J ORG CHEM, V53, P913
[6] Li C. -J., 1997, ORGANIC REACTIONS AQ
[7] Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications
Li, CJ
[J]. TETRAHEDRON, 1996, 52 (16) : 5643 - 5668
[8] Highly stereoselective indium trichloride-catalysed asymmetric aldol reaction of formaldehyde and a glucose-derived silyl enol ether in water
Loh, TP
Chua, GL
Vittal, JJ
Wong, MW
[J]. CHEMICAL COMMUNICATIONS, 1998, (08) : 861 - 862
[9] Novel one-pot mannich-type reaction in water:: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters
Loh, TP
Wei, LL
[J]. TETRAHEDRON LETTERS, 1998, 39 (3-4) : 323 - 326
[10] LUBINEAU A, 1998, ORGANIC SYNTHESIS WA

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