Asymmetric Syntheses of (2R,3S)-3-Hydroxyproline and (2S,3S)-3-Hydroxyproline

被引：12

作者：

Davies, Stephen G. ^{[1
]}

Fletcher, Ai M. ^{[1
]}

Linsdall, Sean M. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Mansfield Rd, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 13期

关键词：

ALPHA-AMINO-ACIDS; PYRROLIZIDINE ALKALOIDS; TRADING N; 3-HYDROXYPROLINE; TRANS-3-HYDROXY-L-PROLINE; CIS; (+)-CIS-(2R; 3S)-3-HYDROXYPROLINE; CIS-(2R; TRANS-3-HYDROXY-D-PROLINE; CONSTITUENT;

D O I：

10.1021/acs.orglett.8b01736

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two synthetic routes have been developed for the asymmetric syntheses of (2R,3S)- and (2S,3S)-3-hydroxyproline. The key synthetic step in each of these strategies is the conversion of protected alpha, delta-dihydroxy-beta-amino esters (either 2,3-anti- or 2,3-syn-configured) into beta, delta-dihydroxy-alpha-amino esters (protected forms thereof), via the intermediacy of the corresponding aziridinium ions. The products of these stereospecific rearrangements were then cyclized and deprotected to afford (2R,3S)-3-hydroxyproline and (2S,3S)-3-hydroxyproline as single diastereoisomers (>99:1 dr) in >26% overall yield.

引用

页码：4135 / 4139

页数：5

共 43 条

[1]

Baiz CR, 2013, ULTRAFAST INFRARED VIBRATIONAL SPECTROSCOPY, P361

[2] EXPEDIENT SYNTHESES OF (+)-CIS-(2R,3S)-3-HYDROXYPROLINE AND (-)-(1S,5S)-2-OXA-6-AZABICYCLO[3.3.0]OCTAN-3-ONE (THE GEISSMAN-WAISS LACTONE) - FORMAL ENANTIOSELECTIVE SYNTHESES OF (-)-RETRONECINE AND RELATED PYRROLIZIDINE ALKALOIDS [J].

COOPER, J ;

GALLAGHER, PT ;

KNIGHT, DW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (08) :509-510

[3] BAKERS-YEAST REDUCTIONS OF BETA-OXOPYRROLIDINECARBOXYLATES - SYNTHESIS OF (+)-CIS-(2R,3S)-3-HYDROXYPROLINE AND (-)-(1S,5S)-GEISSMAN-WAISS LACTONE, A USEFUL PRECURSOR TO PYRROLIZIDINE ALKALOIDS [J].

COOPER, J ;

GALLAGHER, PT ;

KNIGHT, DW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (12) :1313-1317

[4] Trading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acids [J].

Davies, Stephen G. ;

Fletcher, Ai M. ;

Greenaway, Catherine J. ;

Kennedy, Matthew S. ;

Mayer, Christoph ;

Roberts, Paul M. ;

Thomson, James E. .

TETRAHEDRON, 2018, 74 (38) :5049-5061

[5] Trading N and O. Part 3: Synthesis of 1,2,3,4-tetrahydroisoquinolines from α-hydroxy-β-amino esters [J].

Davies, Stephen G. ;

Fletcher, Ai M. ;

Frost, Aileen B. ;

Kennedy, Matthew S. ;

Roberts, Paul M. ;

Thomson, James E. .

TETRAHEDRON, 2016, 72 (17) :2139-2163

[6] Asymmetric Synthesis of Substituted anti-β-Fluorophenylalanines [J].

Davies, Stephen G. ;

Fletcher, Ai M. ;

Frost, Aileen B. ;

Roberts, Paul M. ;

Thomson, James E. .

ORGANIC LETTERS, 2015, 17 (09) :2254-2257

[7] Stereospecific Cyclization Strategies for α,ε-Dihydroxy-β-amino Esters: Asymmetric Syntheses of Imino and Amino Sugars [J].

Davies, Stephen G. ;

Foster, Emma M. ;

Lee, James A. ;

Roberts, Paul M. ;

Thomson, James E. .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (20) :9686-9698

[8] Trading N and O. Part 2: Exploiting aziridinium intermediates for the synthesis of β-hydroxy-α-amino acids [J].

Davies, Stephen G. ;

Fletcher, Ai M. ;

Frost, Aileen B. ;

Roberts, Paul M. ;

Thomson, James E. .

TETRAHEDRON, 2014, 70 (35) :5849-5862

[9] Asymmetric Syntheses of (-)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach [J].

Davies, Stephen G. ;

Figuccia, Aude L. A. ;

Fletcher, Ai M. ;

Roberts, Paul M. ;

Thomson, James E. .

ORGANIC LETTERS, 2013, 15 (08) :2042-2045

[10] The conjugate addition of enantiomerically pure lithium amides as chiral ammonia equivalents part II: 2005-2011 [J].

Davies, Stephen G. ;

Fletcher, Ai M. ;

Roberts, Paul M. ;

Thomson, James E. .

TETRAHEDRON-ASYMMETRY, 2012, 23 (15-16) :1111-1153

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