Novel preparation of (-)-4-hydroxycyclohex-2-enone: reaction of 4-hydroxycyclohex-2-enone and 4-hydroxycyclopent-2-enone with some thiols

被引:15
作者
Bickley, JF
Evans, P
Meek, A
Morgan, BS
Roberts, SM
机构
[1] Univ Manchester, CoEBio3, Manchester M60 1QD, Lancs, England
[2] Univ Dublin Trinity Coll, Dept Chem, Dublin 2, Ireland
[3] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
关键词
D O I
10.1016/j.tetasy.2006.01.002
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new route to (R)-4-hydroxycyclohex-2-enone from cyclohexanedione monoketal (27% yield) commences with reaction of the ketal with nitrosobenzene catalysed by L-proline. 4-Hydroxycyclohex-2-enone and 4-hydroxycyclopent-2-enone react with thiols to afford the corresponding syn-disubstituted cycloalkanones. (c) 2006 Published by Elsevier Ltd.
引用
收藏
页码:355 / 362
页数:8
相关论文
共 23 条
[1]   An efficient approach to either enantiomer of trans-cyclohex-2-ene-1,4-diol [J].
Alibés, R ;
de March, P ;
Figueredo, M ;
Font, J ;
Marjanet, G .
TETRAHEDRON-ASYMMETRY, 2004, 15 (07) :1151-1155
[2]   SYNTHESIS OF 2 USEFUL, ENANTIOMERICALLY PURE DERIVATIVES OF (S)-4-HYDROXY-2-CYCLOHEXENONE [J].
AUDIA, JE ;
BOISVERT, L ;
PATTEN, AD ;
VILLALOBOS, A ;
DANISHEFSKY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3738-3740
[3]  
BAXTER AD, 1986, CHEM IND-LONDON, P510
[4]   Reactions of some cyclopentenones with selected cysteine derivatives and biological activities of the product thioethers [J].
Bickley, JF ;
Ciucci, A ;
Evans, P ;
Roberts, SM ;
Ross, N ;
Santoro, MG .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (12) :3221-3227
[5]  
CARRENO MC, 1990, TETRAHEDRON LETT, V31, P6653
[6]   TOTAL SYNTHESES OF ML-236A AND COMPACTIN BY COMBINING THE LACTONIC (SILYL) ENOLATE REARRANGEMENT AND ALDEHYDE-DIENE CYCLOCONDENSATION TECHNOLOGIES [J].
DANISHEFSKY, SJ ;
SIMONEAU, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2599-2604
[7]   Synthesis of 4-azacyclopent-2-enones and 5,5-dialkyl-4-azacyclopent-2-enones [J].
Dauvergne, J ;
Happe, AM ;
Jadhav, V ;
Justice, D ;
Matos, MC ;
McCormack, PJ ;
Pitts, MR ;
Roberts, SM ;
Singh, SK ;
Snape, TJ ;
Whittall, J .
TETRAHEDRON, 2004, 60 (11) :2559-2567
[8]  
DAUVERGNE J, 2004, TETRAHEDRON, V60, P2557
[9]   New, highly efficient syntheses of rac-, (R)- and (S)-4-hydroxy-2-cyclohexenone [J].
de March, P ;
Escoda, M ;
Figueredo, M ;
Font, J ;
García-García, E ;
Rodríguez, S .
TETRAHEDRON-ASYMMETRY, 2000, 11 (22) :4473-4483
[10]   Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase [J].
Deardorff, DR ;
Amador, RB ;
Morton, JW ;
Kim, HY ;
Taniguchi, CM ;
Balbuena, AA ;
Warren, SA ;
Fanous, V ;
Choe, SWT .
TETRAHEDRON-ASYMMETRY, 1999, 10 (11) :2139-2152