N-tritylprolinal:: An efficient building block for the stereoselective synthesis of proline-derived amino alcohols

被引：30

作者：

Bejjani, J ^{[1
]}

Chemla, F ^{[1
]}

Audouin, M ^{[1
]}

机构：

[1] Univ Paris 06, Chim Organ Lab, UMR 7611, F-75252 Paris 05, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 25期

关键词：

D O I：

10.1021/jo034976g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Tritylprolinal (prepared in four steps from L-proline) shows a very high Felkin diastereoselectivity in its reaction with various nucleophiles, leading to a straightforward and highly stereoselective access to syn-proline-derived amino alcohols.

引用

页码：9747 / 9752

页数：6

共 56 条

[1] Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes [J].

Andrés, JM ;

Pedrosa, R ;

Pérez, A ;

Pérez-Encabo, A .

TETRAHEDRON, 2001, 57 (40) :8521-8530

[2] A formal synthesis of pumiliotoxin 251D, via a highly diastereoselective addition of a titanium homoenolate to an L-proline derivative [J].

Barrett, AGM ;

Damiani, F .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1410-1411

[3] ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONE AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONE FROM BOC-L-PROLINAL AND (S)-[(ETA-5-C5H5)FE(CO)(PPH3)(AC)] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)(AC)], RESPECTIVELY [J].

BECKETT, RP ;

DAVIES, SG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (03) :160-161

[4] ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] [J].

BECKETT, RP ;

DAVIES, SG ;

MORTLOCK, AA .

TETRAHEDRON-ASYMMETRY, 1992, 3 (01) :123-136

[5] HIGHLY REGIOSELECTIVE AND DIASTEREOSELECTIVE FRIEDEL-CRAFTS ALKYLATION OF PHENOLS WITH ALPHA-AMINO ALDEHYDES - SYNTHESIS OF OPTICALLY-ACTIVE EPHEDRINE-LIKE COMPOUNDS [J].

BIGI, F ;

CASNATI, G ;

SARTORI, G ;

ARALDI, G ;

BOCELLI, G .

TETRAHEDRON LETTERS, 1989, 30 (09) :1121-1124

[6]

DEKONING H, 1973, RECL TRAV CHIM PAY B, V92, P237

[7] NEW INHIBITORS OF RENIN THAT CONTAIN NOVEL PHOSPHOSTATINE LEU-VAL REPLACEMENTS [J].

DELLARIA, JF ;

MAKI, RG ;

STEIN, HH ;

COHEN, J ;

WHITTERN, D ;

MARSH, K ;

HOFFMAN, DJ ;

PLATTNER, JJ ;

PERUN, TJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :534-542

[8] CHIRAL, CYCLIC AMINO ALDEHYDES IN THE BAYLIS-HILLMAN REACTION - A ROUTE TO SPHINGOSINE ANALOGS [J].

DREWES, SE ;

KHAN, AA ;

ROWLAND, K .

SYNTHETIC COMMUNICATIONS, 1993, 23 (02) :183-188

[9]

Fehr C, 2000, ANGEW CHEM INT EDIT, V39, P569, DOI 10.1002/(SICI)1521-3773(20000204)39:3<569::AID-ANIE569>3.0.CO

[10]

2-8

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