Highly alkyl-selective addition to ketones with magnesium ate complexes derived from Grignard reagents

被引：76

作者：

Hatano, M ^{[1
]}

Matsumura, T ^{[1
]}

Ishihara, K ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 04期

关键词：

D O I：

10.1021/ol047685i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient alkyl-selective addition to ketones with magnesium ate complexes derived from Grignard reagents and alkyllithiums is described, The nucleophilicity of R in R3MgLi is remarkably increased compared to that of the original RU or RMgX, while the basicity of R3MgLi is decreased. Furthermore, a highly R-selective addition to ketones is demonstrated using RMe2MgLi in place of R3MgLi.

引用

页码：573 / 576

页数：4

共 27 条

[1] STEREOSELECTIVE ORGANOMETALLIC ALKYLATION REACTIONS .3. ATE COMPLEX ADDITION TO CYCLIC AND BICYCLIC KETONES
ASHBY, EC
CHAO, LC
LAEMMLE, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (22) : 3258 - 3263
[2] Tributylmagnesium ate complex-mediated bromine-magnesium exchange of bromoquinolines:: a convenient access to functionalized quinolines
Dumouchel, S
Mongin, F
Trécourt, F
Quéguiner, G
[J]. TETRAHEDRON LETTERS, 2003, 44 (10) : 2033 - 2035
[3] Henry Gilman: American pioneer in the rise of organometallic chemistry in modern science and technology
Eisch, JJ
[J]. ORGANOMETALLICS, 2002, 21 (25) : 5439 - 5463
[4] Tributylmagnesium ate complex-mediated novel bromine-magnesium exchange reaction for selective monosubstitution of dibromoarenes
Iida, T
Wada, T
Tomimoto, K
Mase, T
[J]. TETRAHEDRON LETTERS, 2001, 42 (29) : 4841 - 4844
[5] ORGANOCERIUM REAGENTS - NUCLEOPHILIC-ADDITION TO EASILY ENOLIZABLE KETONES
IMAMOTO, T
SUGIURA, Y
TAKIYAMA, N
[J]. TETRAHEDRON LETTERS, 1984, 25 (38) : 4233 - 4236
[6] CERIUM CHLORIDE-PROMOTED NUCLEOPHILIC-ADDITION OF GRIGNARD-REAGENTS TO KETONES AN EFFICIENT METHOD FOR THE SYNTHESIS OF TERTIARY ALCOHOLS
IMAMOTO, T
TAKIYAMA, N
NAKAMURA, K
[J]. TETRAHEDRON LETTERS, 1985, 26 (39) : 4763 - 4766
[7] REACTIONS OF CARBONYL-COMPOUNDS WITH GRIGNARD-REAGENTS IN THE PRESENCE OF CERIUM CHLORIDE
IMAMOTO, T
TAKIYAMA, N
NAKAMURA, K
HATAJIMA, T
KAMIYA, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4392 - 4398
[8] Selective halogen-magnesium exchange reaction via organomagnesium ate complex
Inoue, A
Kitagawa, K
Shinokubo, H
Oshima, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) : 4333 - 4339
[9] Inoue A, 2002, CHEM-EUR J, V8, P1730, DOI 10.1002/1521-3765(20020402)8:7<1730::AID-CHEM1730>3.0.CO
[10] 2-6

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