NDLI: Asymmetric Strecker Reaction Catalyzed by a Brønsted Acid

Content Provider	Scilit
Author	Rueping, M. Sugiono, E. Azap, C.
Copyright Year	2006
Description	A highly enantioselective Strecker reaction furnishing N-protected α-amino nitriles is presented. Viable substrates are N-benzyl- and N-para-methoxybenzyl-protected imines derived from both aromatic and heteroaromatic aldehydes. Good to excellent results were obtained with electron-rich as well as electron-deficient starting materials. Aliphatic imines can also be employed, albeit the enantioselectivity is severely reduced [for example, 2-(benzylamino)-3-methylbutyronitrile was obtained in 55% ee]. Screening different catalysts revealed that increasing steric bulk benefits the selectivity of the reaction, while HCN emerged as the reactant and toluene as the solvent of choice.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-941788.pdf
Ending Page	0613
Page Count	1
Starting Page	0613
ISSN	18611958
e-ISSN	1861194X
DOI	10.1055/s-2006-941788
Journal	Synfacts
Issue Number	6
Volume Number	2006
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2006-05-19
Access Restriction	Open
Subject Keyword	Journal: Synfacts Organic Chemistry Strecker Reaction Enantioselectivity
Content Type	Text
Resource Type	Article

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Asymmetric Strecker Reaction Catalyzed by a Brønsted Acid