Asymmetric synthesis of tetrahydrofurans by competitive [1,2]-phenylsulfanyl (PhS) migrations under thermodynamic control

被引:7
作者
Caggiano, L
Fox, DJ
House, D
Jones, ZA
Kerr, F
Warren, S
机构
[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[3] Dyson Perrins Lab, Oxford 0X1 3QY, England
[4] AstraZeneca, Macclesfield SK10 2NA, Cheshire, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 23期
关键词
D O I
10.1039/b208556a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Triols were prepared in enantiomerically enriched form by a short route that included a Sharpless asymmetric dihydroxylation; treatment of these triols with toluene-p-sulfonic acid gave THFs as thermodynamic products.
引用
收藏
页码:2634 / 2645
页数:12
相关论文
共 35 条
[1]   TRANSFORMATION OF CYCLIC ALPHA-PHENYLTHIO ALDEHYDES BY STEREOSELECTIVE ALDOL REACTIONS AND PHENYLTHIO MIGRATION INTO SPIROCYCLIC LACTONES AND ETHERS, AND E-ALLYLIC ALCOHOLS WITH 1,4-RELATED CHIRAL CENTERS [J].
AGGARWAL, VK ;
COLDHAM, I ;
MCINTYRE, S ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02) :451-460
[2]   A study of the stereochemical features of 5-endo-trig iodocyclisations of 2-alkenylcycloalkan-1-ols [J].
Barks, JM ;
Weingarten, GG ;
Knight, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (20) :3469-3476
[3]   Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols [J].
Bedford, SB ;
Bell, KE ;
Bennett, F ;
Hayes, CJ ;
Knight, DW ;
Shaw, DE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (15) :2143-2153
[4]   1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].
CHEN, KM ;
HARDTMANN, GE ;
PRASAD, K ;
REPIC, O ;
SHAPIRO, MJ .
TETRAHEDRON LETTERS, 1987, 28 (02) :155-158
[5]  
COREY EJ, 1975, TETRAHEDRON LETT, P2647
[6]   IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].
CRISPINO, GA ;
JEONG, KS ;
KOLB, HC ;
WANG, ZM ;
XU, DQ ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786
[7]   REARRANGEMENTS OF PHENYLTHIO SUBSTITUTED 1,N-DIOLS WITH TOLUENE-P-SULFONIC ACID AND WITH TOLUENE-P-SULFONYL CHLORIDE [J].
DJAKOVITCH, L ;
EAMES, J ;
JONES, RVH ;
MCINTYRE, S ;
WARREN, S .
TETRAHEDRON LETTERS, 1995, 36 (10) :1723-1726
[8]   Kinetic and thermodynamic control in the stereospecific synthesis of cyclic ethers via phenylsulfanyl (PhS) migration [J].
Eames, J ;
Warren, S .
TETRAHEDRON LETTERS, 1996, 37 (20) :3525-3528
[9]  
Eames J, 1999, SYNLETT, P1211
[10]   An efficient protocol for Sharpless-style racemic dihydroxylation [J].
Eames, J ;
Mitchell, HJ ;
Nelson, A ;
O'Brien, P ;
Warren, S ;
Wyatt, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :1095-1103