Towards α,α-Disubstituted Amino Acids Containing Vicinal Stereocenters via Stereoselective Transition-Metal Catalyzed Allylation

Recent development in the transition metal-catalyzed cyclization reactions for organic syntheses in the author's laboratories is summarized, which includes (i) novel silylcarbocyclizations (SiCaCs) and carbonylative carbotricyclizations, (ii) intramolecular silylformylations and desymmerization of siloxydiynes by sequential double silylformylation, (iii) efficient total synthesis of (+)-prosopinine, (iv) enantioselective desymmetrization of aminodienes, and (iv) new and efficient routes to 1-azabicyclo[x.y.0]alkane amino acids. All these processes are catalyzed by Rh or RhCo complexes, and useful for rapid and efficient construction of a variety of heterocyclic and carbocyclic compounds. Mechanisms of these new carbocyclization and cyclohydrocarbonylation reactions are also discussed.

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ChemInform Abstract: Transition Metal Catalyzed Chlorine Transfer Cyclizations of Carbon- Centered Glycine Radicals; A Novel Synthetic Route to Cyclic α- Amino Acids.

ChemInform ◽

10.1002/chin.199423215 ◽

2010 ◽

Vol 25 (23) ◽

pp. no-no

Author(s):

J. H. UDDING ◽

C. J. M. TUIJP ◽

H. HIEMSTRA ◽

W. N. SPECKAMP

Keyword(s):

Amino Acids ◽

Transition Metal ◽

Synthetic Route ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

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Transition metal catalyzed asymmetric organic synthesis via polymer bound chiral ligands. Synthesis of R amino acids and hydratropic acid by hydrogenation

Journal of the American Chemical Society ◽

10.1021/ja00433a063 ◽

1976 ◽

Vol 98 (17) ◽

pp. 5400-5402 ◽

Cited By ~ 52

Author(s):

Naotake Takaishi ◽

Hirosuke Imai ◽

Christopher A. Bertelo ◽

J. K. Stille

Keyword(s):

Amino Acids ◽

Transition Metal ◽

Organic Synthesis ◽

Chiral Ligands ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

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Transition-metal-catalyzed asymmetric organic synthesis via polymer-attached optically active phosphine ligands. 5. Preparation of amino acids in high optical yield via catalytic hydrogenation

The Journal of Organic Chemistry ◽

10.1021/jo00327a023 ◽

1981 ◽

Vol 46 (14) ◽

pp. 2954-2960 ◽

Cited By ~ 118

Author(s):

Gregory L. Baker ◽

Scott J. Fritschel ◽

John R. Stille ◽

John K. Stille

Keyword(s):

Amino Acids ◽

Transition Metal ◽

Organic Synthesis ◽

Catalytic Hydrogenation ◽

Optically Active ◽

Phosphine Ligands ◽

Optical Yield ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

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Copper-catalyzed N-(hetero)arylation of amino acids in water

RSC Advances ◽

10.1039/c6ra23364c ◽

2016 ◽

Vol 6 (99) ◽

pp. 96762-96767 ◽

Cited By ~ 7

Author(s):

Krishna K. Sharma ◽

Meenakshi Mandloi ◽

Neha Rai ◽

Rahul Jain

Keyword(s):

Amino Acids ◽

Transition Metal ◽

Cost Effective ◽

Environmentally Benign ◽

Cost Effective Method ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

A transition metal-catalyzed, environmentally benign, rapid and cost-effective method for the N-(hetero)arylation of zwitterionic amino acids in water is reported.

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