SmI2-coupling reaction of chiral non-racemic α-bromo-α′-sulfinyl ketones with imines: synthesis of enantiomerically pure 2-methyl-3-amino-1-ol moieties

被引：14

作者：

Barbarotto, Marie ^{[1
]}

Geist, Julie ^{[1
]}

Choppin, Sabine ^{[1
]}

Colobert, Francoise ^{[1
]}

机构：

[1] Univ Strasbourg, ECPM, CNRS, Lab Stereochim,UMR 7509, F-67087 Strasbourg 2, France

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 24期

关键词：

ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SAMARIUM DIIODIDE; MANNICH REACTION; SULFOXIDES; VERSATILE; ACID;

D O I：

10.1016/j.tetasy.2009.11.020

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral non-racemic alpha-bromo-alpha'-sulfinyl ketones were shown to react with imines in the presence of SmI2 to give the corresponding 1,3-aminoketo derivatives with good syn-diastereoselectivity. Further reduction of these adducts either with DIBAL-H only or with DIBAL-H in the presence of Yb(OTf)(3) afforded syn- and anti-2-methyl-3-amino-1-ol moieties, respectively, in good yields and diastereoselectivities. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2780 / 2787

页数：8

共 30 条

[1] Scope and limitations of the nitro-Mannich reaction for the stereoselective synthesis of 1,2-diamines [J].

Anderson, JC ;

Blake, AJ ;

Howell, GP ;

Wilson, C .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :549-555

[2] New versatile fluorinated chiral building blocks: Synthesis and reactivity of optically pure alpha-(fluoroalkyl)-beta-sulfinylenamines [J].

Arnone, A ;

Bravo, P ;

Capelli, S ;

Fronza, G ;

Meille, SV ;

Zanda, M ;

Cavicchio, G ;

Crucianelli, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3375-3387

[3] APPLICATIONS OF CROTYLDIISOPINOCAMPHEYLBORANES IN SYNTHESIS - THE TOTAL SYNTHESIS OF NIKKOMYCIN-B [J].

BARRETT, AGM ;

LEBOLD, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4875-4884

[4] Asymmetric synthesis of α-arylglycinols via additions of lithium methyl p-tolyl sulfoxide to N-(PMP)arylaldimines followed by "non oxidative" Pummerer reaction [J].

Bravo, P ;

Capelli, S ;

Crucianelli, M ;

Guidetti, M ;

Markovsky, AL ;

Meille, SV ;

Soloshonok, VA ;

Sorochinsky, AE ;

Viani, F ;

Zanda, M .

TETRAHEDRON, 1999, 55 (10) :3025-3040

[5] Efficient stereochemical controllers in biaryl Suzuki coupling reactions:: Benzylic carbinols bearing in β-position thioether, dimethylamino, or sulfoxide groups [J].

Broutin, PE ;

Colobert, F .

ORGANIC LETTERS, 2005, 7 (17) :3737-3740

[6] An asymmetric biaryl Suzuki cross-coupling reaction: Stereogenic benzylic carbinols as chiral auxiliaries [J].

Broutin, PE ;

Colobert, F .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (06) :1113-1128

[7] Sulfoxide-directed stereocontrolled access to 2H-chromans:: Total synthesis' of the (S,R,R,R)-enantiomer of the antihypertensive drug nebivolol [J].

Carreno, M. Carmen ;

Hernandez-Torres, Gloria ;

Urbano, Antonio ;

Colobert, Francoise .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (12) :2035-2038

[8] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].

CARRENO, MC .

CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760

[9] STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES [J].

CARRENO, MC ;

RUANO, JLG ;

MARTIN, AM ;

PEDREGAL, C ;

RODRIGUEZ, JH ;

RUBIO, A ;

SANCHEZ, J ;

SOLLADIE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2120-2128

[10] Synthesis of new enantiopure gamma-aminoalcohols: Their use as catalysts in the alkylation of benzaldehyde by diethylzinc [J].

Cicchi, S ;

Crea, S ;

Goti, A ;

Brandi, A .

TETRAHEDRON-ASYMMETRY, 1997, 8 (02) :293-301

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