- Ir-Catalyzed Enantioconvergent Synthesis of Diversely Protected Allenylic Amines Employing Ammonia Surrogates
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The first iridium catalyzed, enantioconvergent amination of allenylic carbonates is reported. This process utilizes various commercially available carbamates and sulfonamides to generate allenylic amines including commonly employed protected groups (Boc, Fmoc, Cbz, Ts, Ns) in 62–82 % yield and 87–98 % ee. The products generated through this scalable procedure serve as effective linchpins for the rapid, enantiospecific synthesis of a wide range of complex structures.
- Carreira, Erick M.,Glatz, Fabian,Petrone, David A.
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supporting information
p. 16404 - 16408
(2020/07/27)
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- GRANZYME B DIRECTED IMAGING AND THERAPY
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Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.
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Page/Page column 113
(2019/09/04)
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- Preparation of (S)-1-cyclopropyl-2-methoxyethanamine by a chemoenzymatic route using leucine dehydrogenase
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(S)-1-Cyclopropyl-2-methoxyethanamine is a key chiral intermediate for the synthesis of a corticotropin-releasing factor-1(CRF-1) receptor antagonist. Resolution of the racemic amine by transaminase from Vibrio fluvalis gave a 38% yield of the S-amine wit
- Parker, William L.,Hanson, Ronald L.,Goldberg, Steven L.,Tully, Thomas P.,Goswami, Animesh
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experimental part
p. 464 - 469
(2012/08/08)
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- Practical syntheses of both enantiomers of cyclopropylglycine and of methyl 2-cyclopropyl-2-N-Boc-iminoacetate
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A facile three-step synthesis of racemic cyclopropylglycine in multigram quantities from inexpensive cyclopropyl methyl ketone has been elaborated. Enzymatic hydrolysis of the N-Boc-protected methyl ester of cyclopropylglycine 9 with the inexpensive enzyme papain from Carica papaya affords both enantiomers of cyclopropylglycine (8) with enantiomeric excesses of 99% or better after deprotection under acidic conditions. Furthermore, the new cyclopropyl group-containing building block methyl 2-cyclopropyl-2-N-Boc-iminoacetate (13) was prepared by N-chlorination and subsequent dehydrochlorination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Addition of nucleophiles to 13 offers a ready access to an unusual, orthogonally bisprotected α,α-diamino acid derivative and interesting components of rigid peptide backbones.
- Larionov, Oleg V.,De Meijere, Armin
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p. 1071 - 1078
(2007/10/03)
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- A general, highly enantioselective method for the synthesis of D and L α-amino acids and allylic amines
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Catalytic and enantioselective synthesis of amino acids is a subject of intense interest in the field of asymmetric catalysis. Traditionally, researchers have concentrated their efforts largely on the design and discovery of enantiopure catalysts for the
- Chen, Young K.,Lurain, Alice E.,Walsh, Patrick J.
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p. 12225 - 12231
(2007/10/03)
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- A Versatile Method for the Synthesis of (S)- or (R)-Cycloalkylglycines, (S)- or (R)-N-Heterocyclic and α,β-Unsaturated N-Heterocyclic α-Amino Acids
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Two different types of cyclic α-amino acids, cycloalkylglycines and N-heterocyclic α-amino acids, were prepared in optically pure form from the same chiral synthon 1-(R) (or 1-(S)) simply by altering the quantity or type of base required for anion formation.Elaboration of the heterocyclic intermediate 3 provided α,β-unsaturated N-heterocyclic α-amino acids.
- Pauly, Regine,Sasaki, N. Andre,Potier, Pierre
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p. 237 - 240
(2007/10/02)
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