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author:

Liu, M. (Liu, M..) [1] | Wang, J. (Wang, J..) [2] | Yuan, X. (Yuan, X..) [3] | Jiang, R. (Jiang, R..) [4] | Fu, N. (Fu, N..) [5]

Indexed by:

Scopus

Abstract:

A series of β-lactams containing the ferrocene moiety were synthesized through the Staudinger reaction between ferrocenylketene generated by the thermal Wolff rearrangement of the corresponding diazo ketone and various imines. The stereochemical outcome has been investigated and the trans-products were isolated as the main products, opposite to the reported results by Bonini and coworkers. The absolute configuration of (±)-trans-1,4-diphenyl-3-ferrocenylazetidin-2-one (3c) was determined by X-ray analysis. The stereoselectivity is discussed from the viewpoint of the reaction mechanism. © 2017 Taylor & Francis.

Keyword:

ferrocenyl-ketene; stereoselectivity; thermal Wolff rearrangement; β-Lactams

Community:

  • [ 1 ] [Liu, M.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, China
  • [ 2 ] [Wang, J.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, China
  • [ 3 ] [Yuan, X.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, China
  • [ 4 ] [Jiang, R.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, China
  • [ 5 ] [Fu, N.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, China

Reprint 's Address:

  • [Fu, N.]New Campus of Fuzhou University, University Town, Minhou, 2 Xue Yuan Road, China

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Source :

Synthetic Communications

ISSN: 0039-7911

Year: 2017

Issue: 24

Volume: 47

Page: 2369-2377

1 . 3 7 7

JCR@2017

1 . 8 0 0

JCR@2023

ESI HC Threshold:226

JCR Journal Grade:3

CAS Journal Grade:4

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 5

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 1

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