The aldol reaction of allenolates with aldehydes in the presence of magnesium diiodide (MgI2) as catalyst

被引：21

作者：

Deng, GH ^{[1
]}

Hu, H

Wei, HX

Paré, PW

机构：

[1] GuangXi Univ Nationalities, Dept Chem, Nanning 530006, Peoples R China

[2] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

HELVETICA CHIMICA ACTA | 2003年 / 86卷 / 10期

关键词：

D O I：

10.1002/hlca.200390294

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stereoselective synthesis of (Z)-alpha-(hydroxyalkyl)-beta-iodoacrylates (= (2Z)-2-(hydroxyalkyl)-3-iodoprop-2-enoates) was achieved in a one-pot coupling reaction from methyl prop-2-ynoate, Me3SiI, and an alkanal under mild conditions with MgI2 as catalyst (--> 1-9; see Table and Scheme 1). Baylis-Hillman beta-iodo adducts were generated in excellent yields with high (Z)-selectivity. The conversion of methyl prop-2-ynoate to an active methyl 3-iodo-1-[(trimethylsilyl)oxy]allenolate intermediate in situ followed by carbonyl addition is proposed as the reaction sequence (Schemes 1 and 2).

引用

页码：3510 / 3515

页数：6

共 18 条

[1] 1,4-DIAZOBICYCLO[2.2.2]OCTANE-CATALYZED COUPLING OF ALDEHYDES AND ACTIVATED DOUBLE-BONDS .3. A SHORT AND PRACTICAL SYNTHESIS OF MIKANECIC ACID (4-VINYL-1-CYCLOHEXENE-1,4-DICARBOXYLIC ACID)
HOFFMANN, HMR
RABE, J
[J]. HELVETICA CHIMICA ACTA, 1984, 67 (02) : 413 - 415
[2] ALDOL REACTION OF ALUMINUM ENOLATE RESULTING FROM 1,4-ADDITION OF ME2ALSPH TO ALPHA,BETA-UNSATURATED CARBONYL COMPOUND - ALPHA 1-ACYLETHENYL ANION EQUIVALENT
ITOH, A
OZAWA, S
OSHIMA, K
NOZAKI, H
[J]. TETRAHEDRON LETTERS, 1980, 21 (04) : 361 - 364
[3] The asymmetric catalytic aldol reaction of allenolates with aldehydes using N-fluoroacyl oxazaborolidine as the catalyst
Li, GG
Wei, HX
Phelps, BS
Purkiss, DW
Kim, SH
[J]. ORGANIC LETTERS, 2001, 3 (06) : 823 - 826
[4] A new stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts
Li, GG
Wei, HX
Willis, S
[J]. TETRAHEDRON LETTERS, 1998, 39 (26) : 4607 - 4610
[5] Novel asymmetric C-C bond formation process promoted by Et2AlCl and its application to the stereoselective synthesis of unusual β-branched Baylis-Hillman adducts
Li, GG
Wei, HX
Whittlesey, BR
Batrice, NN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) : 1061 - 1064
[6] TiCl4-Mediated Baylis-Hillman and aldol reactions without the direct use of a Lewis base
Li, GG
Wei, HX
Gao, JJ
Caputo, TD
[J]. TETRAHEDRON LETTERS, 2000, 41 (01) : 1 - 5
[7] Ytterbium(III) triflate-catalyzed asymmetric nucleophilic addition of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p-toluenesulfinimines (thiooxime S-oxides)
Li, GG
Wei, HX
Hook, JD
[J]. TETRAHEDRON LETTERS, 1999, 40 (25) : 4611 - 4614
[8] Vinylalumination of activated carbonyl compounds
Ramachandran, PV
Reddy, MVR
Rudd, MT
[J]. TETRAHEDRON LETTERS, 1999, 40 (04) : 627 - 630
[9] ROTH F, 1992, TETRAHEDRON LETT, V48, P6371
[10] BETA-HALOVINYL KETONES - SYNTHESIS FROM ACETYLENIC KETONES
TANIGUCHI, M
KOBAYASHI, S
NAKAGAWA, M
HINO, T
KISHI, Y
[J]. TETRAHEDRON LETTERS, 1986, 27 (39) : 4763 - 4766

← 1 2 →