Asymmetric Dihydroxylations of 1-Substituted (E)- and (Z)-3-Methylpent-2-en-4-ynes: Full Compliance with the Sharpless Mnemonic Re-established and Embellished

被引：8

作者：

Burghart-Stoll, Heike ^{[1
]}

Boehnke, Oliver ^{[2
]}

Brueckner, Reinhard ^{[1
]}

机构：

[1] Univ Freiburg, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany

[2] Gymnasium Goetheschule, D-37574 Einbeck, Germany

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 05期

关键词：

BETA; GAMMA-UNSATURATED CARBOXYLIC ESTERS; HOMOALLYLIC ALCOHOL DERIVATIVES; CINCHONA ALKALOID CATALYST; ENANTIOSELECTIVE SYNTHESIS; VITAMIN-E; LIGAND CLASS; ALKENES; OLEFINS; CONFIGURATION; BUTENOLIDES;

D O I：

10.1021/ol103063t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric dihydroxylations ("ADs") of the pentenynyl chlorides (E)- and (Z)-1 or the pentenyne-based ester (Z)-3 in the presence of (DHQ)(2)-containing ligands delivered diol stereoisomers (2R,3S)-2, (2R,3R)-2, and (3S,4R)-4, respectively. The ADs of pentenynyl ethers (E)-10 and (Z)-12, respectively, have the same stereochemical preference under analogous conditions; these reattributions correct previous reports of the contrary. The Sharpless mnemonic rationalizes all these results implying that each substrate prefers a Sharpless/Norrby instead of a Chapleur orientation in the transition state.

引用

页码：1020 / 1023

页数：4

共 51 条

[1] Enantioselective synthesis of all of the stereoisomers of (E)-13,14-dihydroxyretinol (DHR) [J].

Alvarez, S ;

Alvarez, R ;

de Lera, AR .

TETRAHEDRON-ASYMMETRY, 2004, 15 (05) :839-846

[2] A new ligand class for the asymmetric dihydroxylation of olefins [J].

Becker, H ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :448-451

[3]

BECKER H, 1996, ANGEW CHEM, V108, P447

[4]

BOHNKE O, 2002, THESIS U FREIBURG, P63

[5]

Bolm C., 2000, Catal. Asymmetric Synth, V2nd, P399

[6] Asymmetric Dihydroxylations of Enynes with a Trisubstituted C=C Bond. An Unprecedented Route to γ-Lactone Building Blocks with a Quaternary Stereocenter [J].

Burghart-Stoll, Heike ;

Kapferer, Tobias ;

Brueckner, Reinhard .

ORGANIC LETTERS, 2011, 13 (05) :1016-1019

[7] First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers [J].

Claudel, S ;

Olszewski, TK ;

Mutzenardt, P ;

Aroulanda, C ;

Coutrot, P ;

Grison, C .

TETRAHEDRON, 2006, 62 (08) :1787-1798

[8] NOVEL TOTAL SYNTHESIS OF (2R,4'R,8'R)-ALPHA-TOCOPHEROL (VITAMIN-E) - CONSTRUCTION OF CHIRAL CHROMANS FROM AN OPTICALLY-ACTIVE, NON-AROMATIC PRECURSOR [J].

COHEN, N ;

LOPRESTI, RJ ;

SAUCY, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (22) :6710-6716

[9] HIGHLY ENANTIOSELECTIVE AND REGIOSELECTIVE CATALYTIC DIHYDROXYLATION OF HOMOALLYLIC ALCOHOL DERIVATIVES [J].

COREY, EJ ;

GUZMANPEREZ, A ;

NOE, MC .

TETRAHEDRON LETTERS, 1995, 36 (20) :3481-3484

[10] THE APPLICATION OF A MECHANISTIC MODEL LEADS TO THE EXTENSION OF THE SHARPLESS ASYMMETRIC DIHYDROXYLATION TO ALLYLIC 4-METHOXYBENZOATES AND CONFORMATIONALLY RELATED AMINE AND HOMOALLYLIC ALCOHOL DERIVATIVES [J].

COREY, EJ ;

GUZMANPEREZ, A ;

NOE, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :10805-10816

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