Convenient synthesis of adamantyl-substituted β -lactams via uncatalyzed staudinger reaction - Details

author：

Liu, M. (Liu, M..) ^[1] | Chen, Y. (Chen, Y..) ^[2] | Fu, N. (Fu, N..) ^[3]

Indexed by：

Scopus

Abstract：

A　series　of　C3-position　adamantyl-substituted　β-lactams　were　synthesized　via　uncatalyzed　Staudinger　reaction　between　adamantylketene　generated　by　thermal　Wolff　rearrangement　of　the　corresponding　diazo　ketone　and　various　imines.　The　stereochemical　outcome　of　the　reaction　was　mainly　the　formation　of　trans-products,　a　result　attributed　to　a　two-step　mechanism　leading　to　the　most　stable　products.　©　2013　Copyright　Taylor　and　Francis　Group,　LLC.

Keyword：

β-lactam; Adamantane; Staudinger reaction; stereoselectivity; thermal Wolff rearrangement

Community：

[ 1 ] [Liu, M.]Ministry of Education Key Laboratory of Analysis and Detection Technology for Food Safety, Department of Chemistry, Qi Shan Campus of Fuzhou University, 2 Xue Yuan Road, Fujian 350108, China
[ 2 ] [Liu, M.]State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, China
[ 3 ] [Chen, Y.]Ministry of Education Key Laboratory of Analysis and Detection Technology for Food Safety, Department of Chemistry, Qi Shan Campus of Fuzhou University, 2 Xue Yuan Road, Fujian 350108, China
[ 4 ] [Chen, Y.]State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, China
[ 5 ] [Fu, N.]Ministry of Education Key Laboratory of Analysis and Detection Technology for Food Safety, Department of Chemistry, Qi Shan Campus of Fuzhou University, 2 Xue Yuan Road, Fujian 350108, China
[ 6 ] [Fu, N.]State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, China

Reprint 's Address：

[Fu, N.]Ministry of Education Key Laboratory of Analysis and Detection Technology for Food Safety, Department of Chemistry, Qi Shan Campus of Fuzhou University, 2 Xue Yuan Road, Fujian 350108, China

Email：

nayan-fu@fzu.edu.cn

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Source ：

Synthetic Communications

ISSN： 0039-7911

Year： 2013

Issue： 7

Volume： 43

Page： 1055-1062

0 . 9 8 4

JCR@2013

1 . 8 0 0

JCR@2023

JCR Journal Grade：3

CAS Journal Grade：4

Cited Count：

WoS CC Cited Count：

SCOPUS Cited Count： 6

ESI Highly Cited Papers on the List： 0 Unfold All

WanFang Cited Count：

Chinese Cited Count：

30 Days PV： 1

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