Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused β-lactams in an organic solvent

被引:85
作者
Forró, E [1 ]
Fulöp, F [1 ]
机构
[1] Univ Szeged, Inst Pharmaceut Chem, H-6701 Szeged, Hungary
关键词
D O I
10.1021/ol034096o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic, beta-lactams in organic media. High enantioselectivity (E > 200) was observed when the Lipolase flipase B from Candida antarctica)-catalyzed reactions were performed with H2O (1 equiv) in dilsopropyl ether at 60 degreesC. The resolved products, obtained in good chemical yield (36-47%), could be easily separated.
引用
收藏
页码:1209 / 1212
页数:4
相关论文
共 52 条
[1]  
Achilles K, 2000, ARCH PHARM, V333, P243, DOI 10.1002/1521-4184(20008)333:8<243::AID-ARDP243>3.3.CO
[2]  
2-F
[3]   Synthesis of optically active α-methylene β-lactams through lipase-catalyzed kinetic resolution [J].
Adam, W ;
Groer, P ;
Humpf, HU ;
Saha-Möller, CR .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4919-4922
[4]   Highly diastereoselective nitrone cycloaddition onto a chiral ketene equivalent: Asymmetric synthesis of cispentacin [J].
Aggarwal, VK ;
Roseblade, SJ ;
Barrell, JK ;
Alexander, R .
ORGANIC LETTERS, 2002, 4 (07) :1227-1229
[5]   Efficient entry to highly functionalized β-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction of 2-azetidinone-tethered nitrones.: Synthetic applications [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM ;
Aly, MF ;
Pardo, C ;
Sáez, E ;
Torres, MR .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7004-7013
[6]   Residue-based control of helix shape in beta-peptide oligomers [J].
Appella, DH ;
Christianson, LA ;
Klein, DA ;
Powell, DR ;
Huang, XL ;
Barchi, JJ ;
Gellman, SH .
NATURE, 1997, 387 (6631) :381-384
[7]  
Bolm C, 2001, SYNLETT, P1875
[8]   Non-peptide αvβ3 antagonists.: Part 5:: Identification of potent RGD mimetics incorporating 2-aryl β-amino acids as aspartic acid replacements [J].
Brashear, KM ;
Hunt, CA ;
Kucer, BT ;
Duggan, ME ;
Hartman, GD ;
Rodan, GA ;
Rodan, SB ;
Leu, CT ;
Prueksaritanont, T ;
Fernandez-Metzler, C ;
Barrish, A ;
Homnick, CF ;
Hutchinson, JH ;
Coleman, PJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (23) :3483-3486
[9]   Total enzymatic resolution of racemic 2-(4-methoxybenzyl)-1-cyclohexanols and 2-(4-methoxybenzyl)-1-cyclopentanols [J].
Brunet, C ;
Zarevucka, M ;
Wimmer, Z ;
Legoy, MD .
ENZYME AND MICROBIAL TECHNOLOGY, 2002, 31 (05) :609-614
[10]   Two-carbon ring expansion of β-lactams via N(1)-C(4) cleavage reactions [J].
Cabell, LA ;
McMurray, JS .
TETRAHEDRON LETTERS, 2002, 43 (14) :2491-2493