A catalytic asymmetric synthesis of 5,5-dimethylproline

被引:19
作者
Elaridi, J [1 ]
Jackson, WR [1 ]
Robinson, AJ [1 ]
机构
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
关键词
D O I
10.1016/j.tetasy.2005.05.003
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The methyl ester derivative of commercially available N-acetyl-allylglycine readily undergoes cross-metathesis with 2-methylbut-2-ene and ruthenium-alkylidene catalyst to afford the prenylglycine derivative. Acid-catalysed cyclisation then affords 5,5-dimethylproline in near quantitative yield and enantioselectivity. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码:2025 / 2029
页数:5
相关论文
共 25 条
[1]   Mechanism and activity of ruthenium olefin metathesis catalysts: The role of ligands and substrates from a theoretical perspective [J].
Adlhart, C ;
Chen, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3496-3510
[2]   Retention of the cis proline conformation in tripeptide fragments of bovine pancreatic ribonuclease A containing a non-natural proline analogue, 5,5-dimethylproline [J].
An, SSA ;
Lester, CC ;
Peng, JL ;
Li, YJ ;
Rothwarf, DM ;
Welker, E ;
Thannhauser, TW ;
Zhang, LS ;
Tam, JP ;
Scheraga, HA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11558-11566
[3]   Protein prosthesis:: A nonnatural residue accelerates folding and increases stability [J].
Arnold, U ;
Hinderaker, MP ;
Köditz, J ;
Golbik, R ;
Ulbrich-Hofmann, R ;
Raines, RT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (25) :7500-7501
[4]   EXPERIMENTS TOWARDS THE SYNTHESIS OF CORRINS .1. THE PREPARATION AND REACTIONS OF SOME DELTA-1- PYRROLINES - A NOVEL PROLINE SYNTHESIS [J].
BONNETT, R ;
CLARK, VM ;
GIDDEY, A ;
TODD, A .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (JUN) :2087-2093
[5]   PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ ;
FEASTER, JE ;
NUGENT, WA ;
HARLOW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138
[6]   Highly regio- and enantioselective catalytic hydrogenation of enamides in conjugated diene systems:: Synthesis and application of γ,δ-unsaturated amino acids [J].
Burk, MJ ;
Allen, JG ;
Kiesman, WF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :657-663
[7]  
COURT JJ, 1996, Patent No. 9616970
[8]   An electronic effect on protein structure [J].
Hinderaker, MP ;
Raines, RT .
PROTEIN SCIENCE, 2003, 12 (06) :1188-1194
[9]   Decomposition of a key intermediate in ruthenium-catalyzed olefin metathesis reactions [J].
Hong, SH ;
Day, MW ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7414-7415
[10]   Non-proline cis peptide bonds in proteins [J].
Jabs, A ;
Weiss, MS ;
Hilgenfeld, R .
JOURNAL OF MOLECULAR BIOLOGY, 1999, 286 (01) :291-304