Facile synthesis of versatile functionalized amino caprolactams using RCM reactions of α-amino acrylamide

Gang Liu; Wan Yi Tai; Yu Lin Li; Fa Jun Nan

doi:10.1016/j.tetlet.2006.03.022

Facile synthesis of versatile functionalized amino caprolactams using RCM reactions of α-amino acrylamide

Gang Liu
, Wan Yi Tai
, Yu Lin Li
, Fa Jun Nan

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

30 Scopus citations

Abstract

We report an efficient synthetic methodology allowing access to functionalized α-amino caprolactams using ring-closing metathesis (RCM). A very high tolerance of α-amino acrylamide RCM precursors toward functional groups is demonstrated. The synthetic pathway is facile, and can be extended to prepare a variety of substituted amino caprolactams in good to excellent yields. These compounds serve as versatile building blocks for the synthesis of some important natural products and their analogues.

Original language	English (US)
Pages (from-to)	3295-3298
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2006.03.022
State	Published - May 8 2006
Externally published	Yes

Keywords

Functionalized lactams
Natural products
Ring-closing metathesis
α-Amino acrylamide
α-Amino α,β-unsaturated caprolactams

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.03.022

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title = "Facile synthesis of versatile functionalized amino caprolactams using RCM reactions of α-amino acrylamide",

abstract = "We report an efficient synthetic methodology allowing access to functionalized α-amino caprolactams using ring-closing metathesis (RCM). A very high tolerance of α-amino acrylamide RCM precursors toward functional groups is demonstrated. The synthetic pathway is facile, and can be extended to prepare a variety of substituted amino caprolactams in good to excellent yields. These compounds serve as versatile building blocks for the synthesis of some important natural products and their analogues.",

keywords = "Functionalized lactams, Natural products, Ring-closing metathesis, α-Amino acrylamide, α-Amino α,β-unsaturated caprolactams",

author = "Gang Liu and Tai, \{Wan Yi\} and Li, \{Yu Lin\} and Nan, \{Fa Jun\}",

note = "Funding Information: This work was supported by the National Natural Science Foundation of China (Grant 30572242) and the Shanghai Commission of Science and Technology (Grant 03dz19228). ",

year = "2006",

month = may,

day = "8",

doi = "10.1016/j.tetlet.2006.03.022",

language = "English (US)",

volume = "47",

pages = "3295--3298",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "19",

}

TY - JOUR

T1 - Facile synthesis of versatile functionalized amino caprolactams using RCM reactions of α-amino acrylamide

AU - Liu, Gang

AU - Tai, Wan Yi

AU - Li, Yu Lin

AU - Nan, Fa Jun

N1 - Funding Information: This work was supported by the National Natural Science Foundation of China (Grant 30572242) and the Shanghai Commission of Science and Technology (Grant 03dz19228).

PY - 2006/5/8

Y1 - 2006/5/8

N2 - We report an efficient synthetic methodology allowing access to functionalized α-amino caprolactams using ring-closing metathesis (RCM). A very high tolerance of α-amino acrylamide RCM precursors toward functional groups is demonstrated. The synthetic pathway is facile, and can be extended to prepare a variety of substituted amino caprolactams in good to excellent yields. These compounds serve as versatile building blocks for the synthesis of some important natural products and their analogues.

AB - We report an efficient synthetic methodology allowing access to functionalized α-amino caprolactams using ring-closing metathesis (RCM). A very high tolerance of α-amino acrylamide RCM precursors toward functional groups is demonstrated. The synthetic pathway is facile, and can be extended to prepare a variety of substituted amino caprolactams in good to excellent yields. These compounds serve as versatile building blocks for the synthesis of some important natural products and their analogues.

KW - Functionalized lactams

KW - Natural products

KW - Ring-closing metathesis

KW - α-Amino acrylamide

KW - α-Amino α,β-unsaturated caprolactams

UR - https://www.scopus.com/pages/publications/33646472886

UR - https://www.scopus.com/pages/publications/33646472886#tab=citedBy

U2 - 10.1016/j.tetlet.2006.03.022

DO - 10.1016/j.tetlet.2006.03.022

M3 - Article

AN - SCOPUS:33646472886

SN - 0040-4039

VL - 47

SP - 3295

EP - 3298

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Facile synthesis of versatile functionalized amino caprolactams using RCM reactions of α-amino acrylamide

Abstract

Keywords

ASJC Scopus subject areas

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