A Protocol for an Asymmetric Synthesis of γ-Amino Acids

被引:20
作者
Reddy, Leleti Rajender [1 ]
Prasad, Kapa [1 ]
Prashad, Mahavir [1 ]
机构
[1] Novartis Pharmaceut, Chem & Analyt Dev, E Hanover, NJ 07936 USA
关键词
TERT-BUTANESULFINYL IMINES; X-RAY-CRYSTAL; BETA-PEPTIDES; NMR-SOLUTION; DESIGN; DERIVATIVES; REDUCTION; PYRROLIDINES; LIGANDS; ESTERS;
D O I
10.1021/jo301177f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and practical method for the asymmetric synthesis of gamma-amino acids from beta,gamma-butenolides by an in situ esterification, condensation, and reduction in a one-pot procedure is described. This method is quite general for the preparation of both enantiomers of aryl or aliphatic gamma-amino acids in high yields. These gamma-amino-acid derivatives were also shown to be versatile synthetic intermediates for further transformations by their conversion to gamma-lactams, delta-amino alcohols, and hydrolysis products in high yields with no racernization.
引用
收藏
页码:6296 / 6301
页数:6
相关论文
共 38 条
[21]   An advance on exploring N-tert-butanesulfinyl imines in asymmetric synthesis of chiral amines [J].
Lin, Guo-Qiang ;
Xu, Ming-Hua ;
Zhong, Yu-Wu ;
Sun, Xing-Wen .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (07) :831-840
[22]   Asymmetric Reduction of Imines with Trichlorosilane, Catalyzed by Sigamide, an Amino Acid-Derived Formamide: Scope and Limitations [J].
Malkov, Andrei V. ;
Vrankova, Kvetoslava ;
Stoncius, Sigitas ;
Kocovsky, Pavel .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :5839-5849
[23]   Asymmetric synthesis of homoallylic amines bearing adjacent stereogenic centers by addition of substituted allylic zinc reagents to N-tert-butanesulfinylimines [J].
Reddy, Leleti Rajender ;
Hu, Bin ;
Prashad, Mahavir ;
Prasad, Kapa .
ORGANIC LETTERS, 2008, 10 (14) :3109-3112
[24]   Rhodium-Catalyzed Asymmetric Arylation of N-(tert-Butanesulfinyl)imines with Sodium Tetraarylborates [J].
Reddy, Leleti Rajender ;
Gupta, Aditya P. ;
Villhauer, Eric ;
Liu, Yugang .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) :1095-1100
[25]   Asymmetric Synthesis of α-Amino Acids by Reduction of N-tert-Butanesulfinyl Ketimine Esters [J].
Reddy, Leleti Rajender ;
Gupta, Aditya P. ;
Liu, Yugang .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) :3409-3415
[26]   A Facile Asymmetric Synthesis of Either Enantiomer of 2-Substituted Pyrrolidines [J].
Reddy, Leleti Rajender ;
Das, Sonia G. ;
Liu, Yugang ;
Prashad, Mahavir .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (07) :2236-2246
[27]   Asymmetric synthesis of 2-substituted pyrrolidines by addition of Grignard reagents to γ-chlorinated N-tert-butanesulfinyl imine [J].
Reddy, Leleti Rajender ;
Prashad, Mahavir .
CHEMICAL COMMUNICATIONS, 2010, 46 (02) :222-224
[28]   Two New Hetero-Spirocyclic γ-Lactam Derivatives from Marine Sediment-derived Fungus Aspergillus sydowi D2-6 [J].
Ren, Hong ;
Liu, Rui ;
Chen, Li ;
Zhu, Tianjiao ;
Zhu, Wei Ming ;
Gu, Qian Qun .
ARCHIVES OF PHARMACAL RESEARCH, 2010, 33 (04) :499-502
[29]   Synthesis and Applications of tert-Butanesulfinamide [J].
Robak, MaryAnn T. ;
Herbage, Melissa A. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (06) :3600-3740
[30]   Structure-based design and synthesis of a potent matrix metalloproteinase-13 inhibitor based on a pyrrolidinone scaffold [J].
Robinson, RP ;
Laird, ER ;
Blake, JF ;
Bordner, J ;
Donahue, KM ;
Lopresti-Morrow, LL ;
Mitchell, PG ;
Reese, MR ;
Reeves, LM ;
Stam, EJ ;
Yocum, SA .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (12) :2293-2296