An efficient resolution of (+/-)-S-methyl-S-phenylsulfoximine with (+)-10-camphorsulfonic acid by the method of half-quantities

被引：130

作者：

Brandt, J ^{[1
]}

Gais, HJ ^{[1
]}

机构：

[1] RHEIN WESTFAL TH AACHEN,INST ORGAN CHEM,D-52056 AACHEN,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(97)00046-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Racemic S-methyl-S-phenylsulfoximine (+/-)-1 can be resolved with only 0.6 equivalents of (+)-camphorsulfonic acid by avoiding any recrystallization to give (+)-1 of greater than or equal to 99% ee in 80% yield and (-)-1 of 97-99% ee in 74% yield. This procedure, which is based on the separation of the diastereomeric salt (+)-1/(+)-CSA and the sulfoximine (-)-1, should be suited for a large scale application. (C) 1997 Elsevier Science Ltd.

引用

页码：909 / 912

页数：4

共 17 条

[1] Barbachyn M. R., 1984, ASYMMETRIC SYNTHESIS, V4, P227
[2] Optically active sulfoximines in enantioselective palladium catalysis
Bolm, C
Kaufmann, D
Zehnder, M
Neuburger, M
[J]. TETRAHEDRON LETTERS, 1996, 37 (23) : 3985 - 3988
[3] REGIOSELECTIVE AND ENANTIOSELECTIVE SUBSTITUTION OF ALLYLIC SULFOXIMINES WITH ORGANOCOPPER REAGENTS - A VERSATILE APPROACH TO OPTICALLY-ACTIVE ISOCARBACYCLINS
BUND, J
GAIS, HJ
ERDELMEIER, I
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) : 1442 - 1444
[4] DITER P, 1995, J ORG CHEM, V60, P8086
[5] Eliel E.L., 1994, Stereochemistry of Organic Compounds
[6] NICKEL-CATALYZED CROSS-COUPLINGS OF ALKENYL AND ALPHA-METALATED ALKENYL SULFOXIMINES WITH ORGANOMETALLICS - STEREOSELECTIVE SYNTHESIS OF CARBACYCLINS
ERDELMEIER, I
GAIS, HJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) : 1125 - 1126
[7] FUSCO R, 1965, CHIM IND-MILAN, V47, P61
[8] Stereoselective hydroxyalkylation of titanated allyl sulfoximines at the alpha- as well as the gamma-position through variation of the titanation reagent
Hainz, R
Gais, HJ
Raabe, G
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (09) : 2505 - 2508
[9] Stereoselective addition of organometallic reagents to N-(tosyl)vinylsulfoximines
Jackson, RFW
Briggs, AD
Brown, PA
Clegg, W
Elsegood, MRJ
Frampton, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (14): : 1673 - 1682
[10] Jacques J., 1991, ENANTIOMERS RACEMATE

← 1 2 →