Lewis acid-catalyzed one-pot crossed Prins cyclizations using allylchlorosilane as allylating agent

Kok Ping Chan; Teck Peng Loh

doi:10.1016/j.tetlet.2004.09.049

Lewis acid-catalyzed one-pot crossed Prins cyclizations using allylchlorosilane as allylating agent

Kok Ping Chan, Teck Peng Loh

National University of Singapore

Research output: Contribution to journal › Article › peer-review

57 Scopus citations

Abstract

A one-pot multi-component Lewis acid-catalyzed Prins cyclization was developed with high yield and selectivity. The crossed 2,4,6-trisubstituted tetrahydropyran products were formed with high stereoselectivity. This catalytic method could also be used with α,β-unsaturated aldehydes affording moderate yields of products. A one-pot multi-component Lewis acid-catalyzed Prins cyclization was developed with high yield and selectivity. The crossed 2,4,6-trisubstituted tetrahydropyran products were formed with high stereoselectivity. This catalytic method could also be used with α,β-unsaturated aldehydes affording moderate yields of products.

Original language	English
Pages (from-to)	8387-8390
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2004.09.049
State	Published - 1 Nov 2004
Externally published	Yes

Keywords

In(OTf)
InCl
Prins cyclization
Tetrahydropyran

Access to Document

10.1016/j.tetlet.2004.09.049

Cite this

@article{d740dbac19894f6587c149f9b9e10512,

title = "Lewis acid-catalyzed one-pot crossed Prins cyclizations using allylchlorosilane as allylating agent",

abstract = "A one-pot multi-component Lewis acid-catalyzed Prins cyclization was developed with high yield and selectivity. The crossed 2,4,6-trisubstituted tetrahydropyran products were formed with high stereoselectivity. This catalytic method could also be used with α,β-unsaturated aldehydes affording moderate yields of products. A one-pot multi-component Lewis acid-catalyzed Prins cyclization was developed with high yield and selectivity. The crossed 2,4,6-trisubstituted tetrahydropyran products were formed with high stereoselectivity. This catalytic method could also be used with α,β-unsaturated aldehydes affording moderate yields of products.",

keywords = "In(OTf), InCl, Prins cyclization, Tetrahydropyran",

author = "Chan, {Kok Ping} and Loh, {Teck Peng}",

year = "2004",

month = nov,

day = "1",

doi = "10.1016/j.tetlet.2004.09.049",

language = "英语",

volume = "45",

pages = "8387--8390",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "45",

}

TY - JOUR

T1 - Lewis acid-catalyzed one-pot crossed Prins cyclizations using allylchlorosilane as allylating agent

AU - Chan, Kok Ping

AU - Loh, Teck Peng

PY - 2004/11/1

Y1 - 2004/11/1

N2 - A one-pot multi-component Lewis acid-catalyzed Prins cyclization was developed with high yield and selectivity. The crossed 2,4,6-trisubstituted tetrahydropyran products were formed with high stereoselectivity. This catalytic method could also be used with α,β-unsaturated aldehydes affording moderate yields of products. A one-pot multi-component Lewis acid-catalyzed Prins cyclization was developed with high yield and selectivity. The crossed 2,4,6-trisubstituted tetrahydropyran products were formed with high stereoselectivity. This catalytic method could also be used with α,β-unsaturated aldehydes affording moderate yields of products.

AB - A one-pot multi-component Lewis acid-catalyzed Prins cyclization was developed with high yield and selectivity. The crossed 2,4,6-trisubstituted tetrahydropyran products were formed with high stereoselectivity. This catalytic method could also be used with α,β-unsaturated aldehydes affording moderate yields of products. A one-pot multi-component Lewis acid-catalyzed Prins cyclization was developed with high yield and selectivity. The crossed 2,4,6-trisubstituted tetrahydropyran products were formed with high stereoselectivity. This catalytic method could also be used with α,β-unsaturated aldehydes affording moderate yields of products.

KW - In(OTf)

KW - InCl

KW - Prins cyclization

KW - Tetrahydropyran

UR - http://www.scopus.com/inward/record.url?scp=5144229083&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2004.09.049

DO - 10.1016/j.tetlet.2004.09.049

M3 - 文章

AN - SCOPUS:5144229083

SN - 0040-4039

VL - 45

SP - 8387

EP - 8390

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

Lewis acid-catalyzed one-pot crossed Prins cyclizations using allylchlorosilane as allylating agent

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this