Enantioselective Pummerer-type rearrangement by reaction of O-silylated ketene acetal with enantiopure alpha-substituted sulfoxides

被引：7

作者：

Kita, Y ^{[1
]}

Shibata, N ^{[1
]}

Fukui, S ^{[1
]}

Bando, M ^{[1
]}

Fujita, S ^{[1
]}

机构：

[1] OTSUKA PHARMACEUT CO LTD,TOKUSHIMA INST NEW DRUG RES 2,TOKUSHIMA 77101,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 12期

关键词：

D O I：

10.1039/a702020a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral non-racemic alpha-substituted sulfoxides have-been allowed to-react with O-silylated ketene acetals: in the presence of a catalytic amount of ZnI2 in THF to give chiral non-racemic alpha-siloxy sulfides in >99% ee. This is the highest enantioselectivity reported to date for the Pummerer reaction.

引用

页码：1763 / 1767

页数：5

共 25 条

[1] ENANTIOSELECTIVE PUMMERER-TYPE REARRANGEMENT BY REACTION OF O-SILYLATED KETENE ACETAL WITH ENANTIOPURE ALPHA-SUBSTITUTED SULFOXIDES
KITA, Y
SHIBATA, N
FUKUI, S
FUJITA, S
TETRAHEDRON LETTERS, 1994, 35 (52) : 9733 - 9736
[2] Enantioselective Pummerer-type rearrangement by reaction of O-silylated ketene acetal with enantiopure a-substituted sulfoxides
J Chem Soc Perkin Trans 1, 12 (1763):
[3] THE CHEMISTRY OF O-SILYLATED KETENE ACETAL - PUMMERER REARRANGEMENT OF SULFOXIDES INTO ALPHA-SILOXYSULFIDES
KITA, Y
YASUDA, H
TAMURA, O
ITOH, F
TAMURA, Y
TETRAHEDRON LETTERS, 1984, 25 (41) : 4681 - 4682
[4] Enantioselective additive pummerer-type reaction in chiral, non-racemic vinyl sulfoxides induced by O-silylated ketene acetal
Shibata, N
Fujimori, C
Fujita, S
Kita, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1996, 44 (05) : 892 - 894
[5] Mechanistic studies of a Pummerer-type reaction in acyclic and rigid cyclic sulfoxides induced by O-silylated ketene acetal
J Chem Soc Perkin Trans 1, (2829):
[6] Asymmetric pummerer-type reaction induced by O-silylated ketene acetals
Kita, Yasuyuki
Shibata, Norio
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 1994, 52 (09):
[7] ASYMMETRIC PUMMERER-TYPE REACTION INDUCED BY O-SILYLATED KETENE ACETALS
KITA, Y
SHIBATA, N
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1994, 52 (09) : 746 - 753
[8] FIRST HIGHLY ASYMMETRIC PUMMERER-TYPE REACTION IN CHIRAL, NON-RACEMIC ACYCLIC SULFOXIDES INDUCED BY O-SILYLATED KETENE ACETAL
KITA, Y
SHIBATA, N
YOSHIDA, N
FUJITA, S
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (22): : 3335 - 3341
[9] Asymmetric pummerer-type reactions induced by O-silylated ketene acetals
Kita, Y
Shibata, N
SYNLETT, 1996, (04) : 289 - 296
[10] THE 1ST HIGHLY ASYMMETRIC PUMMERER-TYPE REACTION IN CHIRAL ACYCLIC SULFOXIDES - CHEMISTRY OF O-SILYLATED KETENE ACETALS
KITA, Y
SHIBATA, N
YOSHIDA, N
TETRAHEDRON LETTERS, 1993, 34 (25) : 4063 - 4066

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