Asymmetric halo-Mannich-type reaction provides access to pyrrolidines and β-proline derivatives

Cody Timmons; Li Guo; Junying Liu; John F. Cannon; Guigen Li

doi:10.1021/jo0509051

Asymmetric halo-Mannich-type reaction provides access to pyrrolidines and β-proline derivatives

Cody Timmons, Li Guo, Junying Liu, John F. Cannon, Guigen Li

Chemistry and Biochemistry

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

12 Scopus citations

Abstract

A new halo-Mannich-type reaction is reported using cyclopropyl carbonyl-derived enolates and sulfonyl-protected imines. Chiral oxazolidinones auxiliaries were found to be effective for completely controlling the stereochemistry of the products. Variations in the oxazolidinone, protecting group, and imine components show this to be a quite general reaction. The initial iodo-Mannich products were found to be readily cyclized in the presence of triethylamine to afford the resulting protected pyrrolidines, which could be readily deprotected under standard conditions.

Original language	English
Pages (from-to)	7634-7639
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	70
Issue number	19
DOIs	https://doi.org/10.1021/jo0509051
State	Published - Sep 16 2005

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title = "Asymmetric halo-Mannich-type reaction provides access to pyrrolidines and β-proline derivatives",

abstract = "A new halo-Mannich-type reaction is reported using cyclopropyl carbonyl-derived enolates and sulfonyl-protected imines. Chiral oxazolidinones auxiliaries were found to be effective for completely controlling the stereochemistry of the products. Variations in the oxazolidinone, protecting group, and imine components show this to be a quite general reaction. The initial iodo-Mannich products were found to be readily cyclized in the presence of triethylamine to afford the resulting protected pyrrolidines, which could be readily deprotected under standard conditions.",

author = "Cody Timmons and Li Guo and Junying Liu and Cannon, {John F.} and Guigen Li",

year = "2005",

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doi = "10.1021/jo0509051",

language = "English",

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journal = "Journal of Organic Chemistry",

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T1 - Asymmetric halo-Mannich-type reaction provides access to pyrrolidines and β-proline derivatives

AU - Timmons, Cody

AU - Guo, Li

AU - Liu, Junying

AU - Cannon, John F.

AU - Li, Guigen

PY - 2005/9/16

Y1 - 2005/9/16

N2 - A new halo-Mannich-type reaction is reported using cyclopropyl carbonyl-derived enolates and sulfonyl-protected imines. Chiral oxazolidinones auxiliaries were found to be effective for completely controlling the stereochemistry of the products. Variations in the oxazolidinone, protecting group, and imine components show this to be a quite general reaction. The initial iodo-Mannich products were found to be readily cyclized in the presence of triethylamine to afford the resulting protected pyrrolidines, which could be readily deprotected under standard conditions.

AB - A new halo-Mannich-type reaction is reported using cyclopropyl carbonyl-derived enolates and sulfonyl-protected imines. Chiral oxazolidinones auxiliaries were found to be effective for completely controlling the stereochemistry of the products. Variations in the oxazolidinone, protecting group, and imine components show this to be a quite general reaction. The initial iodo-Mannich products were found to be readily cyclized in the presence of triethylamine to afford the resulting protected pyrrolidines, which could be readily deprotected under standard conditions.

UR - http://www.scopus.com/inward/record.url?scp=24944487185&partnerID=8YFLogxK

U2 - 10.1021/jo0509051

DO - 10.1021/jo0509051

M3 - Article

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AN - SCOPUS:24944487185

SN - 0022-3263

VL - 70

SP - 7634

EP - 7639

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Asymmetric halo-Mannich-type reaction provides access to pyrrolidines and β-proline derivatives

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