One-pot tandem enantioselective hydrogenationhydroformylation synthesis of cyclic a-amino acids

Five- and six-membered cyclic amino acids can be prepared in good yield with high ee (>95%) via tandem rhodium-DuPHOS catalysed asymmetric hydrogenation followed by a rhodium-catalysed hydroformylation–cyclisation sequence in a single pot. The synthesis can be achieved using Rh-DuPHOS as the sole catalyst.

[1]  M. Beller,et al.  ChemInform Abstract: Highly Selective Catalyst Systems for the Hydroformylation of Internal Olefins to Linear Aldehydes. , 2002 .

[2]  W. R. Jackson,et al.  Hydrogenation of nitroarenes bearing aldehyde containing side chains over palladium and platinum catalysts: a new route to medium and large heterocyclic compounds☆ , 2001 .

[3]  B. Breit,et al.  Domino Hydroformylation/Knoevenagel/Hydrogenation Reactions , 2001 .

[4]  H. Y. Li,et al.  Expedient asymmetric synthesis of all four isomers of N,N'-protected 2,3-diaminobutanoic acid. , 2001, The Journal of organic chemistry.

[5]  H. Y. Li,et al.  Highly enantioselective synthesis of alpha,beta-diaminopropanoic acid derivatives using a catalytic asymmetric hydrogenation approach. , 2001, Journal of Organic Chemistry.

[6]  B. Breit,et al.  Domino Hydroformylation-Wittig Reactions. , 1999, Angewandte Chemie.

[7]  W. R. Jackson,et al.  A Hydroformylation Route to Diazabicycloalkanes and Oxazabicycloalkanes Containing Medium and Large Rings , 1999 .

[8]  M. M. Cook,et al.  Use of Phase-Transfer Catalysis in Borohydride Reductions: Review and New Ideas , 1998 .

[9]  M. Burk,et al.  Highly Regio- and Enantioselective Catalytic Hydrogenation of Enamides in Conjugated Diene Systems: Synthesis and Application of γ,δ-Unsaturated Amino Acids , 1998 .

[10]  W. R. Jackson,et al.  Rhodium-catalysed hydroformylation and carbonylation of N-alkenyl-1,3-diaminopropanes , 1997 .

[11]  Stephen Hanessian,et al.  Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics , 1997 .

[12]  A. Parsons.  Recent developments in kainoid amino acid chemistry , 1996 .

[13]  M. Eguchi,et al.  New and Efficient Route to Pipecolic Acid Derivatives by Means of Rh-Catalyzed Intramolecular Cyclohydrocarbonylation , 1995 .

[14]  Barry M. Trost,et al.  Atom Economy—A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way , 1995 .

[15]  B. M. Trost.  Atomökonomische Synthesen – eine Herausforderung in der Organischen Chemie: die Homogenkatalyse als wegweisende Methode , 1995 .

[16]  Richard L. Harlow,et al.  Preparation and use of C2-symmetric bis(phospholanes): production of .alpha.-amino acid derivatives via highly enantioselective hydrogenation reactions , 1993 .

[17]  S. Buchwald,et al.  Practical, high-yield, regioselective, rhodium-catalyzed hydroformylation of functionalized .alpha.-olefins , 1993 .

[18]  H. Takahata,et al.  A short, practical synthesis of the ant venom alkaloid, three (3R,5S,8aS)-3-alkyl-5-methylindolizidines , 1993 .

[19]  I. Ojima,et al.  Amide-directed hydrocarbonylation of N-alkenylamides and α-alkenyllactams , 1991 .

[20]  W. R. Jackson,et al.  The stereochemistry of organometallic compounds: XXXVI. Rhodium-catalysed reactions of unsaturated amines with hydrogen and carbon monoxide. A new synthesis of 2-piperidinones☆☆☆ , 1991 .

[21]  Robert M. Williams,et al.  General synthesis of .beta.,.gamma.-alkynylglycine derivatives , 1990 .

[22]  E. Toone,et al.  Enzymes in organic synthesis. 40. Evaluation of the enantioselectivity of the pig liver esterase catalyzed hydrolyses of racemic piperidine carboxylic acid esters , 1987 .

[23]  M. Whittaker,et al.  Asymmetric synthesis towards (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the California red scale pheromone , 1985 .

[24]  A. Mancuso,et al.  Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride , 1978 .

[25]  U. Zoller,et al.  Amidoalkylation of mercaptans with glyoxylic acid derivatives , 1975 .