+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Copper(II)salen catalysed, asymmetric synthesis of alpha,alpha-disubstituted amino acids



Copper(II)salen catalysed, asymmetric synthesis of alpha,alpha-disubstituted amino acids



Tetrahedron 60(8): 1849-1861



Cu(salen) complex 1 was found to be a versatile catalyst for the asymmetric alkylation of a range of enolates derived from alpha-amino acids, leading to alpha,alpha-disubstituted amino acids. The enantioselectivity of the process decreases as the size of the amino acid sidechain increases, but functionalized amino acids such as allylglycine and aspartic acid are substrates for the process. Benzylic bromides are found to be more enantioselective alkylating agents than propargylic bromides.

Please choose payment method:






(PDF emailed within 1 workday: $29.90)

Accession: 011903531

Download citation: RISBibTeXText


Related references

Influence of aromatic substituents, on metal(II)salen catalysed, asymmetric synthesis of alpha-methyl alpha-amino acids. Tetrahedron 60(28): 5919-5930, 2004

Regioselective nucleophilic ring opening reactions of 2,2-disubstituted aziridines - the asymmetric synthesis of alpha,alpha-disubstituted amino acids. Tetrahedron 52(40): 13035-13050, 1996

Asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acids using (S,S)-cyclohexane-1,2-diol as a chiral auxiliary. Journal of Organic Chemistry 66(8): 2667-2673, 2001

Asymmetric synthesis of monosubstituted and alpha alpha disubstituted alpha amino acids via diastereoselective glycine enolate alkylations. Journal of the American Chemical Society 113(24): 9276-9286, 1991

Recent approaches towards the asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acids. Organic and Biomolecular Chemistry 5(3): 406-430, 2007

Organocatalytic asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acids and derivatives. Journal of the American Chemical Society 130(36): 12031, 2008

Asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acids by diastereoselective alkylation of camphor-based tricyclic iminolactone. Journal of Organic Chemistry 71(12): 4364-4373, 2006

Asymmetric 1,4-addition of oxazolones to nitroalkenes by bifunctional cinchona alkaloid thiourea organocatalysts: synthesis of alpha,alpha-disubstituted alpha-amino acids. Chemistry 14(35): 10958-10966, 2008

Asymmetric synthesis of alpha,alpha-disubstituted amino acids by diastereoselective functionalization of enantiopure phenyloxazinones, derivatives of asymmetric Strecker reaction products of aldehydes. Tetrahedron 57(30): 6361-6366, 23 July, 2001

Proline-catalysed asymmetric amination of alpha,alpha-disubstituted aldehydes: synthesis of configurationally stable enantioenriched alpha-aminoaldehydes. Chemical Communications 2003(19): 2448-2449, 2003

Catalytic, asymmetric synthesis of alpha,alpha-disubstituted amino acids. Tetrahedron Letters 44(10): 2045-2048, 3 March, 2003

Asymmetric synthesis of alpha,beta-disubstituted-alpha-amino acids via direct alkylation of chiral amino acid derivatives with racemic sec-alkyl bromides. Abstracts of Papers American Chemical Society 221(1-2): ORGN 16, 2001

Asymmetric synthesis of amines and alpha,alpha-disubstituted amino acids from tert-butanesulfinyl ketimines. Abstracts of Papers American Chemical Society 219(1-2): ORGN 695, 2000

Asymmetric synthesis of pre-protected alpha,alpha-disubstituted amino acids from tert-butanesulfinyl ketimines. Tetrahedron Letters 42(8): 1433-1436, 19 February, 2001

Synthesis of enantiopure alpha,alpha-disubstituted amino acids from the asymmetric Strecker reaction products of aldehydes. Organic Letters 2(16): 2515-2517, 2000