Asymmetric Mannich reaction between (S)-N-(tert-butanesulfinyl)-3,3,3-trifluoroacetaldimine and malonic acid derivatives. Stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids

被引：40

作者：

Shibata, Norio ^{[1
]}

Nishimine, Takayuki ^{[1
]}

Shibata, Naoyuki ^{[1
]}

Tokunaga, Etsuko ^{[1
]}

Kawada, Kosuke ^{[2
]}

Kagawa, Takumi ^{[2
]}

Luis Acena, Jose ^{[3
]}

Sorochinsky, Alexander E. ^{[3
,4
,5
]}

Soloshonok, Vadim A. ^{[3
,4
]}

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan

[2] TOSOH F TECH Inc, Res Lab, Yamaguchi 7460006, Japan

[3] Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, San Sebastian 20018, Spain

[4] Basque Fdn Sci, IKERBASQUE, Bilbao 48011, Spain

[5] Natl Acad Sci Ukraine, Inst Bioorgan Chem & Petrochem, UA-02094 Kiev, Ukraine

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 09期

关键词：

BETA-AMINO-ACIDS; CRYSTAL-STRUCTURE ANALYSIS; STEREOSELECTIVE-SYNTHESIS; ENOLATE; SULFINIMINES; BASE; PHENYLACETATE; REFORMATSKY; REAGENTS; COMPLEX;

D O I：

10.1039/c3ob42425a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Inorganic as well as organic base catalysis was found to be effective for diastereoselective Mannich additions of malonic acid derivatives to (S-S)-N-(tert-butanesulfinyl)-3,3,3-trifluoroacetaldimine. In the presence of catalytic amounts of inorganic bases, n-BuLi or DMAP, the reaction gives the corresponding (R,S-S)-beta-aminomalonates in good yield and with diastereoselectivity up to 9/1 dr. In contrast, phosphazene bases favour the formation of the (S,S-S)-diastereomer with selectivities as high as 99/1. Simple choosing of an appropriate base catalyst for the Mannich addition reaction allowed us to obtain enantiomerically pure (R)- or (S)-configured 3-amino-4,4,4-trifluorobutanoic acids after hydrolysis and decarboxylation of the corresponding beta-aminomalonates.

引用

页码：1454 / 1462

页数：9

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