Boc-(2S,4S)-4-phenylpyrrolidine-2-carboxylic acid
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Boc-(2S,4S)-4-phenylpyrrolidine-2-carboxylic acid

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Category
BOC-Amino Acids
Catalog number
BAT-007913
CAS number
96314-29-3
Molecular Formula
C16H21NO4
Molecular Weight
291.34
Boc-(2S,4S)-4-phenylpyrrolidine-2-carboxylic acid
IUPAC Name
(2S,4S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenylpyrrolidine-2-carboxylic acid
Synonyms
(2S,4S)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid; (2S,4S)-Boc-4-phenyl-pyrrolidine-2-carboxylic acid; (2S,4S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenylpyrrolidine-2-carboxylic acid
Appearance
White to off-white powder
Purity
≥ 95% (HPLC)
Density
1.196±0.06 g/cm3 (Predicted)
Melting Point
157-160 °C
Boiling Point
441.5±45.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C16H21NO4/c1-16(2,3)21-15(20)17-10-12(9-13(17)14(18)19)11-7-5-4-6-8-11/h4-8,12-13H,9-10H2,1-3H3,(H,18,19)/t12-,13+/m1/s1
InChI Key
JDAQDIQHICLYKH-OLZOCXBDSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1CC(CC1C(=O)O)C2=CC=CC=C2
1. Development of a rapid, room-temperature dynamic kinetic resolution for efficient asymmetric synthesis of alpha-aryl amino acids
Jianfeng Hang, Hongming Li, Li Deng Org Lett. 2002 Sep 19;4(19):3321-4. doi: 10.1021/ol026660l.
[reaction: see text] A rapid, highly efficient and general dynamic kinetic resolution (DKR) of racemic alpha-aryl UNCAs with the dual-function catalysis of modified cinchona alkaloid was accomplished at room temperature. This DKR led to the development of a highly enantioselective catalytic method for the practical synthesis of a wide range of alpha-aryl and alpha-heteroaryl amino acids in 89-92% ee and 86-95% yield from racemic UNCAs.
2. A highly diastereoselective and enantioselective synthesis of polysubstituted pyrrolidines via an organocatalytic dynamic kinetic resolution cascade
Tao Cheng, Sixuan Meng, Yong Huang Org Lett. 2013 Apr 19;15(8):1958-61. doi: 10.1021/ol4006129. Epub 2013 Apr 8.
Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50-95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.
3. Diastereo- and enantioselective anti-selective hydrogenation of α-amino-β-keto ester hydrochlorides and related compounds using transition-metal-chiral-bisphosphine catalysts
Yasumasa Hamada Chem Rec. 2014 Apr;14(2):235-50. doi: 10.1002/tcr.201300032. Epub 2014 Feb 18.
This review describes our recent works on the diastereo- and enantioselective synthesis of anti-β-hydroxy-α-amino acid esters using transition-metal-chiral-bisphosphine catalysts. A variety of transition metals, namely ruthenium (Ru), rhodium (Rh), iridium (Ir), and nickel (Ni), in combination with chiral bisphosphines, worked well as catalysts for the direct anti-selective asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides, yielding anti-β-hydroxy-α-amino acid esters via dynamic kinetic resolution (DKR) in excellent yields and diastereo- and enantioselectivities. The Ru-catalyzed asymmetric hydrogenation of α-amino-β-ketoesters via DKR is the first example of generating anti-β-hydroxy-α-amino acids. Complexes of iridium and axially chiral bisphosphines catalyze an efficient asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides via dynamic kinetic resolution. A homogeneous Ni-chiral-bisphosphine complex also catalyzes an efficient asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides in an anti-selective manner. As a related process, the asymmetric hydrogenation of the configurationally stable substituted α-aminoketones using a Ni catalyst via DKR is also described.
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