Synthesis 2016; 48(19): 3287-3300
DOI: 10.1055/s-0035-1562429
paper
© Georg Thieme Verlag Stuttgart · New York

4-Amino-1-allenylsilanes from 4-Aminopropargylic Acetates through a Silylzincation/Elimination Sequence

Valentin N. Bochatay
,
Zeina Neouchy
,
Fabrice Chemla*
,
Franck Ferreira*
,
Olivier Jackowski
,
Alejandro Pérez-Luna*
Further Information

Publication History

Received: 24 March 2016

Accepted after revision: 18 April 2016

Publication Date:
13 June 2016 (eFirst)

In memory to Professor Jean Normant for his outstanding contribution to organometallic chemistry

Abstract

4-Aminopropargylic acetates afford 4-amino-1-allenylsilanes upon reaction with the lithium (triorganosilyl)zincate (PhMe2Si)3ZnLi. The reaction is both stereoselective and stereospecific and proceeds through syn-silylzincation of the carbon–carbon triple bond followed by subsequent anti-β-elimination of the acetate group.

Supporting Information

 
  • References

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