The potential of sulfimides as chiral acyl anion equivalents

被引：7

作者：

Smith, G ^{[1
]}

Sparey, TJ ^{[1
]}

Taylor, PC ^{[1
]}

机构：

[1] UNIV WARWICK,DEPT CHEM,COVENTRY CV4 7AL,W MIDLANDS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 04期

关键词：

D O I：

10.1039/p19960000313

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of the tosyl imides 6 and 8 of 1,3-dithiane and 1,3,5-trithiane with sodium hydride and alkyl iodides in DMF yields anti alkylated products in all cases, In the case of the trithiane imide 8, both mono- and di-alkylation is observed, Preparation of cyclic sulfimide analogues of Eliel's oxathiane is shown to be problematic, but a new class of O,S-acetals, namely 4-bromophenylthiomethyl (BPTM) ethers, is introduced as a replacement for their troublesome phenylthiomethyl (PTM) analogues.

引用

页码：313 / 317

页数：5

共 29 条

[1] ANION REACTIONS OF 1,3-DITHIANE 1,3-DIOXIDE WITH CARBONYL-COMPOUNDS - HIGH DIASTEREOSELECTIVITY WITH AROMATIC-ALDEHYDES UNDER CONDITIONS OF EQUILIBRIUM CONTROL
AGGARWAL, VK
FRANKLIN, R
MADDOCK, J
EVANS, GR
THOMAS, A
MAHON, MF
MOLLOY, KC
RICE, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) : 2174 - 2182
[2] CHIRAL, BISFUNCTIONALIZATION OF SUBSTRATES - A POWERFUL STRATEGY FOR THE ASYMMETRIC-SYNTHESIS OF C2 SYMMETRIAL COMPOUNDS AND ITS APPLICATION TO THE SYNTHESIS OF ENANTIOMERICALLY PURE TRANS-1,3-DITHIANE 1,3-DIOXIDE
AGGARWAL, VK
EVANS, G
MOYA, E
DOWDEN, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) : 6390 - 6391
[3] AGGARWAL VK, 1981, J PRAKT CHEM, V323, P939
[4] ADDITION OF ORGANOMETALLIC REAGENTS TO ACYLOXATHIANES - DIASTEREOSELECTIVITY AND MECHANISTIC CONSIDERATION
BAI, X
ELIEL, EL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) : 5166 - 5172
[5] ASYMMETRIC-SYNTHESIS OF EPOXIDES USING CHIRAL SULFIMIDES
BAIRD, CP
TAYLOR, PC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (08) : 893 - 894
[6] RELATIVE REACTIVITIES OF VARIOUS SULFIDES, SELENIDES AND HALIDES TOWARDS SH2 ATTACK BY TRIBUTYLTIN RADICALS
BECKWITH, ALJ
PIGOU, PE
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (01) : 77 - 87
[7] A NOVEL AND CONVENIENT SYNTHESIS OF BIS[ARYLTHIO]METHANES
CAMPBELL, MM
JIGAJINNI, VB
MACLEAN, KA
WIGHTMAN, RH
[J]. TETRAHEDRON LETTERS, 1980, 21 (34) : 3305 - 3306
[8] REGIOSELECTIVITY OF METALATION OF 1,3-DITHIOLANES AND 1,3-DITHIOLANE 1-OXIDES
CAREY, FA
DAILEY, OD
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1981, 10 (02): : 169 - 174
[9] STEREOSELECTIVITY OF OXIDATION OF 2-SUBSTITUTED-1,3-DITHIOLANES
CAREY, FA
DAILEY, OD
FROMUTH, TE
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1981, 10 (02): : 163 - 168
[10] COREY EJ, 1975, TETRAHEDRON LETT, P3269

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