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Synthesis 2011(6): 919-923  
DOI: 10.1055/s-0030-1258447
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Dimethylsulfoxide-Promoted Strecker Reaction of N-Tosylaldimines with Cyanoformate

Santosh T. Kadam, Ponnaboina Thirupathi, Sung Soo Kim*
Department of Chemistry, Inha University, Incheon 402-751, South Korea
Fax: +82(32)8675604; e-Mail: sungsoo@inha.ac.kr;
Further Information

Publication History

Received 24 December 2010
Publication Date:
24 February 2011 (online)

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Abstract

A metal-free method for performing the Strecker reaction of N-tosylaldimines with ethyl cyanoformate in dimethylsulf­oxide (DMSO) has been developed. Various types of N-tosyl­-aldimines undergo the cyanation to provide the N-protected α-amino nitriles. This uncatalyzed protocol requires neither elevated temperature nor high pressure for the cyanations.

Key words

N-tosylaldimine - ethyl cyanoformate - α-amino nitriles - Strecker reaction

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16

We tried to isolate the intermediate 11 (R in 7 is 4-MeC6H4; Scheme  [²] ) after 1 h of reaction time before and after work-up procedure. Under these conditions, we observed the formation of 9b instead of intermediate 11. This may mean that a small amount of moisture in the reaction mixture is sufficient to convert 11 into 9.