A new method for the synthesis of unsymmetrical bis-aldols by the samarium(II) iodide-mediated aldol reaction of aldehydes with aryl or alkyl oxiranyl ketones

被引：25

作者：

Mukaiyama, T ^{[1
]}

Arai, H ^{[1
]}

Shiina, I ^{[1
]}

机构：

[1] Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Toyko 1628601, Japan

来源：

CHEMISTRY LETTERS | 2000年 / 05期

关键词：

D O I：

10.1246/cl.2000.580

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Unsymmetrical alkyl or aryl 2-hydroxy-1(1-hydroxyalkyl)-alkyl ketones (bis-aldols) were synthesized by the samarium(II) iodide-mediated aldol reaction of aldehydes with alkyl or aryl oxiranyl ketones. Bis-aldols were formed via the aldol reaction of aldehydes with samarium enolates generated by epoxy-fragmentation of oxiranyl ketones using two moles of samarium(II) iodide.

引用

页码：580 / 581

页数：2

共 11 条

[1] A new method for the synthesis of β-amino-β′-hydroxy ketones by the samarium(II) iodide-mediated aldol reaction of aldehydes with aryl or alkyl aziridinyl ketones
Mukaiyama, T
Ogawa, Y
Kuroda, K
CHEMISTRY LETTERS, 2004, 33 (11) : 1472 - 1473
[2] A new and convenient method for the preparation of cyclooctanone containing bis-aldol skeleton by samarium(II) iodide-mediated intramolecular aldol cyclization of ω-oxiranyl keto octanal
Pudhom, K
Arai, H
Yamane, K
Mukaiyama, T
CHEMISTRY LETTERS, 2002, (01) : 82 - 83
[3] Highly stereoselective Samarium(II) iodide-mediated aldol reactions of acylaziridines with aldehydes
Ogawa, Y
Kuroda, K
Mukaiyama, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2005, 78 (07) : 1309 - 1333
[4] Stereoselective synthesis of δ-Amino-β′,γ-hydroxy-β,γ-unsaturated esters by the samarium(II) iodide-mediated aldol reaction of aldehydes with γ,δ-aziridiny-α,β-unsaturated esters
Ogawa, Y
Kuroda, K
Mukaiyama, T
CHEMISTRY LETTERS, 2005, 34 (03) : 372 - 373
[5] Stereoselective synthesis of 19-hydroxytaxoid by utilizing samarium(II) iodide-mediated double aldol cyclization
Ogawa, Y
Kuroda, K
Matsuo, J
Mukaiyama, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2005, 78 (04) : 677 - 697
[6] Enantioselective synthesis of C11-C17 segment of mycinolide IV using samarium(II) iodide-mediated aldol reaction
Ogawa, Y
Kuroda, K
Mukaiyama, T
CHEMISTRY LETTERS, 2005, 34 (05) : 698 - 699
[7] Germanium(II)-mediated reductive cross-aldol reaction of aldehydes: Synthesis of aldols with diastereocontrolled quaternary carbon centers
Tanaka, Shin-ya
Yasuda, Makoto
Baba, Akio
SYNLETT, 2007, (11) : 1720 - 1724
[8] SYNTHESIS OF ALPHA-HYDROXY KETONES BY SAMARIUM(II) IODIDE-MEDIATED COUPLING OF ORGANIC HALIDES, AN ISOCYANIDE, AND CARBONYL-COMPOUNDS
MURAKAMI, M
KAWANO, T
ITO, H
ITO, Y
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06): : 1458 - 1465
[9] NEW SYNTHESIS OF UNSYMMETRICAL DIARYL KETONES BY REACTION OF ARYL IODIDES WITH ARYLMERCURY(II) HALIDES IN PRESENCE OF NICKEL CARBONYL
RHEE, I
RYANG, M
WATANABE, T
OMURA, H
MURAI, S
SONODA, N
SYNTHESIS-STUTTGART, 1977, (11): : 776 - 777
[10] NEW SEQUENTIAL CARBON-CARBON BOND FORMING REACTIONS - A SAMARIUM(II) IODIDE MEDIATED VINYLOGOUS BARBIER REACTION FOLLOWED BY AN ALDOL REACTION
CURRAN, DP
WOLIN, RL
SYNLETT, 1991, (05) : 317 - 318

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