Synthesis of 3,4-Disubstituted Piperidines by Carbonyl Ene and Prins Cyclizations : A switch in Diastereoselectivity between Lewis and Bronsted acid catalysts

[No Value] [No Value]; Perdip Singh Bahia; John Snaith

Synthesis of 3,4-Disubstituted Piperidines by Carbonyl Ene and Prins Cyclizations : A switch in Diastereoselectivity between Lewis and Bronsted acid catalysts

[No Value] [No Value], Perdip Singh Bahia, John Snaith

Chemistry

Research output: Contribution to journal › Article

41 Citations (Scopus)

Abstract

[GRAPHIC] A novel diastereoselective approach to cis and trans 3,4-disubstituted piperidines is described. Carbonyl ene cyclization of aldehydes 6a-e catalyzed by the Lewis acid methyl aluminum dichloride in refluxing chloroform affords trans piperidines 8a-e with diastereomeric ratios of up to 93:7. By contrast, Prins cyclization of 6a-e catalyzed by hydrochloric acid at low temperatures affords cis products 7a-e with diastereomeric ratios of up to 98:2.

Original language	English
Pages (from-to)	3727-3730
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	21
Publication status	Published - 1 Jan 2002

Cite this

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title = "Synthesis of 3,4-Disubstituted Piperidines by Carbonyl Ene and Prins Cyclizations : A switch in Diastereoselectivity between Lewis and Bronsted acid catalysts",

abstract = "[GRAPHIC] A novel diastereoselective approach to cis and trans 3,4-disubstituted piperidines is described. Carbonyl ene cyclization of aldehydes 6a-e catalyzed by the Lewis acid methyl aluminum dichloride in refluxing chloroform affords trans piperidines 8a-e with diastereomeric ratios of up to 93:7. By contrast, Prins cyclization of 6a-e catalyzed by hydrochloric acid at low temperatures affords cis products 7a-e with diastereomeric ratios of up to 98:2.",

author = "{[No Value]}, {[No Value]} and Bahia, {Perdip Singh} and John Snaith",

year = "2002",

month = jan,

day = "1",

language = "English",

volume = "4",

pages = "3727--3730",

journal = "Organic Letters",

publisher = "American Chemical Society",

number = "21",

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T1 - Synthesis of 3,4-Disubstituted Piperidines by Carbonyl Ene and Prins Cyclizations : A switch in Diastereoselectivity between Lewis and Bronsted acid catalysts

AU - [No Value], [No Value]

AU - Bahia, Perdip Singh

AU - Snaith, John

PY - 2002/1/1

Y1 - 2002/1/1

N2 - [GRAPHIC] A novel diastereoselective approach to cis and trans 3,4-disubstituted piperidines is described. Carbonyl ene cyclization of aldehydes 6a-e catalyzed by the Lewis acid methyl aluminum dichloride in refluxing chloroform affords trans piperidines 8a-e with diastereomeric ratios of up to 93:7. By contrast, Prins cyclization of 6a-e catalyzed by hydrochloric acid at low temperatures affords cis products 7a-e with diastereomeric ratios of up to 98:2.

AB - [GRAPHIC] A novel diastereoselective approach to cis and trans 3,4-disubstituted piperidines is described. Carbonyl ene cyclization of aldehydes 6a-e catalyzed by the Lewis acid methyl aluminum dichloride in refluxing chloroform affords trans piperidines 8a-e with diastereomeric ratios of up to 93:7. By contrast, Prins cyclization of 6a-e catalyzed by hydrochloric acid at low temperatures affords cis products 7a-e with diastereomeric ratios of up to 98:2.

M3 - Article

VL - 4

SP - 3727

EP - 3730

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Synthesis of 3,4-Disubstituted Piperidines by Carbonyl Ene and Prins Cyclizations : A switch in Diastereoselectivity between Lewis and Bronsted acid catalysts

Abstract

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