Convenient Synthesis of Adamantyl-Substituted beta-Lactams via Uncatalyzed Staudinger Reaction - Details

author：

Liu, Mingshun (Liu, Mingshun.) ^[1] | Chen, Yaqing (Chen, Yaqing.) ^[2] | Fu, Nanyan (Fu, Nanyan.) ^[3] (Scholars：傅南雁)

Indexed by：

Scopus SCIE

Abstract：

A　series　of　C3-position　adamantyl-substituted　beta-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.

Keyword：

Adamantane ss-lactam Staudinger reaction stereoselectivity thermal Wolff rearrangement

Community：

[ 1 ] [Liu, Mingshun]Fuzhou Univ, Minist Educ, Key Lab Anal & Detect Technol Food Safety, Fuzhou 350108, Fujian, Peoples R China
[ 2 ] [Chen, Yaqing]Fuzhou Univ, Minist Educ, Key Lab Anal & Detect Technol Food Safety, Fuzhou 350108, Fujian, Peoples R China
[ 3 ] [Fu, Nanyan]Fuzhou Univ, Minist Educ, Key Lab Anal & Detect Technol Food Safety, Fuzhou 350108, Fujian, Peoples R China
[ 4 ] [Liu, Mingshun]Fuzhou Univ, Dept Chem, Fuzhou 350108, Fujian, Peoples R China
[ 5 ] [Chen, Yaqing]Fuzhou Univ, Dept Chem, Fuzhou 350108, Fujian, Peoples R China
[ 6 ] [Fu, Nanyan]Fuzhou Univ, Dept Chem, Fuzhou 350108, Fujian, Peoples R China
[ 7 ] [Liu, Mingshun]Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[ 8 ] [Chen, Yaqing]Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[ 9 ] [Fu, Nanyan]Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

Reprint 's Address：

傅南雁
[Fu, Nanyan]Fuzhou Univ, Minist Educ, Key Lab Anal & Detect Technol Food Safety, Qi Shan Campus,2 Xue Yuan Rd,Univ Town, Fuzhou 350108, Fujian, Peoples R China

Email：

nayan_fu@fzu.edu.cn

Show more details

Version：

Convenient synthesis of adamantyl-substituted β -lactams via uncatalyzed staudinger reaction
2013，Synthetic Communications

Related Keywords：

One-pot synthesis of trans--lactams from ferrocenylketene generated by thermal Wolff rearrangement
2017，SYNTHETIC COMMUNICATIONS
Improving the C-beta Stereoselectivity of L-Threonine Aldolase for the Synthesis of L-threo-4-Methylsulfonylphenylserine by Modulating the Substrate-Binding Pocket To Control the Orientation of the Substrate Entrance
2021，CHEMISTRY-A EUROPEAN JOURNAL
Substituent Position-Controlled Stereoselectivity in Enzymatic Reduction of Diaryl- and Aryl(heteroaryl)methanones
2019，ADVANCED SYNTHESIS & CATALYSIS
Rational design on loop regions for precisely regulating flexibility of catalytic center to mitigate overoxidation of prazole sulfides by Baeyer-Villiger monooxygenase
2024，BIOORGANIC CHEMISTRY

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

ESI Discipline： CHEMISTRY;

JCR Journal Grade：3

CAS Journal Grade：4

Cited Count：

WoS CC Cited Count： 5

SCOPUS Cited Count： 6

ESI Highly Cited Papers on the List： 0 Unfold All

WanFang Cited Count：

Chinese Cited Count：

30 Days PV： 1

Affiliated Colleges：

化学学院本学院/部未明确归属的数据

Get Fulltext

DOI Library Discovery Baidu Scholar Search Web of Science

Type
Departments

All Years Choose Year From to