Functionalization of α,β-unsaturated esters and ketones: A facile and highly stereoselective one-pot approach to N-protected α,β-dehydroamino acid derivatives

Dianjun Chen; Li Guo; Junying Liu; Sameer Kirtane; John F. Cannon; Guigen Li

doi:10.1021/ol050002u

Functionalization of α,β-unsaturated esters and ketones: A facile and highly stereoselective one-pot approach to N-protected α,β-dehydroamino acid derivatives

Dianjun Chen, Li Guo, Junying Liu, Sameer Kirtane, John F. Cannon, Guigen Li

Chemistry and Biochemistry

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

64 Scopus citations

Abstract

(Chemical Equation Presented) A new, facile, and highly stereoselective protocol toward α,β-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of α,β-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples.

Original language	English
Pages (from-to)	921-924
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	5
DOIs	https://doi.org/10.1021/ol050002u
State	Published - Mar 3 2005

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title = "Functionalization of α,β-unsaturated esters and ketones: A facile and highly stereoselective one-pot approach to N-protected α,β-dehydroamino acid derivatives",

abstract = "(Chemical Equation Presented) A new, facile, and highly stereoselective protocol toward α,β-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of α,β-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples.",

author = "Dianjun Chen and Li Guo and Junying Liu and Sameer Kirtane and Cannon, {John F.} and Guigen Li",

year = "2005",

month = mar,

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doi = "10.1021/ol050002u",

language = "English",

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journal = "Organic Letters",

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T1 - Functionalization of α,β-unsaturated esters and ketones

T2 - A facile and highly stereoselective one-pot approach to N-protected α,β-dehydroamino acid derivatives

AU - Chen, Dianjun

AU - Guo, Li

AU - Liu, Junying

AU - Kirtane, Sameer

AU - Cannon, John F.

AU - Li, Guigen

PY - 2005/3/3

Y1 - 2005/3/3

N2 - (Chemical Equation Presented) A new, facile, and highly stereoselective protocol toward α,β-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of α,β-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples.

AB - (Chemical Equation Presented) A new, facile, and highly stereoselective protocol toward α,β-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of α,β-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples.

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U2 - 10.1021/ol050002u

DO - 10.1021/ol050002u

M3 - Article

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AN - SCOPUS:15044365017

SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Functionalization of α,β-unsaturated esters and ketones: A facile and highly stereoselective one-pot approach to N-protected α,β-dehydroamino acid derivatives

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