Synthesis and trimethylaluminum additions on γ-hydroxy-δ-sulfinyl and sulfonyl enoates

被引:9
作者
Carreño, MC
Sanz-Cuestat, MJ
Colobert, F
Solladié, G
机构
[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
[2] Univ Strasbourg, Lab Stereochim Associe, CNRS, ECPM, F-67087 Strasbourg 2, France
关键词
D O I
10.1021/ol048577z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective synthesis of epimeric (R)- and (S)-gamma-hydroxy-delta-p-tolylsulfinyl (or sulfonyl) enoates is reported. Reaction with AlMe3 occurred exclusively at the ester goup allowing a clean and high-yielding access to enantiopure 1,4-diols bearing a tertiary carbinol.
引用
收藏
页码:3537 / 3540
页数:4
相关论文
共 41 条
[1]   STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUND ADDITION TO KETONES [J].
ASHBY, EC ;
LAEMMLE, JT .
CHEMICAL REVIEWS, 1975, 75 (04) :521-546
[2]   SHORT AND EFFICIENT SYNTHESIS OF (R)-4-HYDROXY-4-METHYL CYCLOHEXENONE [J].
BUENO, AB ;
CARRENO, MC ;
RUANO, JLG ;
FISCHER, J .
TETRAHEDRON LETTERS, 1995, 36 (21) :3737-3740
[3]   STEREOSELECTIVE HYDRIDE REDUCTIONS OF CHIRAL 2-P-TOLYLSULFINYLCYCLOALKANONES [J].
BUENO, AB ;
CARRENO, M ;
RUANO, JLG ;
PENA, B ;
RUBIO, A ;
HOYOS, MA .
TETRAHEDRON, 1994, 50 (31) :9355-9364
[4]  
Carreño MC, 2002, ANGEW CHEM INT EDIT, V41, P2755, DOI 10.1002/1521-3773(20020802)41:15<2755::AID-ANIE2755>3.0.CO
[5]  
2-A
[6]   Studies of diastereoselectivity in conjugate addition of organoaluminum reagents to (R)-[(p-tolylsulfinyl)methyl] quinols and derivatives [J].
Carreño, MC ;
González, MP ;
Ribagorda, M ;
Houk, KN .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3687-3693
[7]   STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES [J].
CARRENO, MC ;
RUANO, JLG ;
MARTIN, AM ;
PEDREGAL, C ;
RODRIGUEZ, JH ;
RUBIO, A ;
SANCHEZ, J ;
SOLLADIE, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2120-2128
[8]   Diastereoselective uncatalyzed conjugate addition of organoaluminum reagents: Efficient desymmetrization of (R)-[(p-tolylsulfinyl)methyl]quinols [J].
Carreno, MC ;
Gonzalez, MP ;
Ribagorda, M ;
Fischer, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :6758-6759
[9]   STEREOSELECTIVE REACTIONS OF ALME3 WITH CHIRAL ACYCLIC BETA-KETOSULFOXIDES [J].
CARRENO, MC ;
RUANO, JLG ;
MAESTRO, MC ;
GONZALEZ, MP ;
BUENO, AB ;
FISCHER, J .
TETRAHEDRON, 1993, 49 (47) :11009-11018
[10]   Synthesis and antiproliferative activity of side-chain unsaturated and homologated analogs of 1,25-dihydroxyvitamin D2 (24E)-(1S)-24-dehydro-24a-homo-1,25-dihydroxyergocalciferol and congeners [J].
Chodynski, M ;
Wietrzyk, J ;
Marcinkowska, E ;
Opolski, A ;
Szelejewski, W ;
Kutner, A .
STEROIDS, 2002, 67 (09) :789-798