Enantioselective insertion of metal carbenes into N-H bonds: A potentially versatile route to chiral amine derivatives

Angewandte Chemie - International Edition

Volumn 46, Issue 48, 2007, Pages 9148-9150

  Moody, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Amino acids; Asymmetric synthesis; Carbenes; Diazo compounds; Insertion

Indexed keywords

AMINES; ENANTIOSELECTIVITY; HYDROGEN BONDS; LIGANDS; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; CHIRAL LIGANDS; DIAZO COMPOUNDS;

CARBON;

EID: 37349027263     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703016     Document Type: Review

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23. Note added in proof: Very recently Lee and Fu have reported a further major advance in enantioselective carbene N-H insertion reactions (E. C. Lee, G. C. Fu, J. Am. Chem. Soc. 2007, 129, 12066): Using a copper/planar chiral ferrocene bipyridine catalyst, they achieved excellent enantioselectivities with tert-butyl aryldiazoacetates and benzyl or tert-butyl carbamates as the N-H components. This development immediately addresses one of the limitations of the aforementioned work by Zhou and co-workers in that the nitrogen substituent (Boc or Z) is now readily removable by standard deprotections methods. Hence a range of Boc- or Z-protected arylglycine tert-butyl esters can be prepared in 80-98% ee by catalytic asymmetric N-H insertion.