First enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine via proline catalyzed α-aminooxylation of aldehyde and Pd-catalyzed ether-directed aza-Claisen rearrangement

被引：4

作者：

Ahuja, Brij Bhushan ^{[1
]}

Sudalai, Arumugam ^{[1
]}

机构：

[1] CSIR, Chem Engn & Proc Dev Div, Natl Chem Lab, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 10-11期

关键词：

CHYMOTRYPSIN INHIBITOR; VIOMYCIN BIOSYNTHESIS; ELASTASE INHIBITOR; REVISED STRUCTURE; CLAVAMINIC ACID; CAPREOMYCIN; ORIGIN; CHYMOSTATIN; OLEFINATION; CONVERSION;

D O I：

10.1016/j.tetasy.2015.03.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A concise enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine with an overall yield of 10.9% and 98% ee, starting from commercially available 1,4-butanediol in ten linear steps has been achieved. The key chiral inducing steps are D-proline catalyzed sequential alpha-aminooxylation/Horner-Wadsworth-Emmons olefination of an aldehyde and the subsequent diastereoselective MOM-ether-directed Pd-catalyzed aza-Claisen rearrangement of allylic trichloroacetimidate. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：548 / 552

页数：5

共 39 条

[1] A concise enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid via proline catalyzed α-aminooxylation of aldehydes and Pd-catalyzed ether directed aza-Claisen rearrangements [J].

Ahuja, Brij Bhushan ;

Sudalai, Arumugam .

TETRAHEDRON-ASYMMETRY, 2015, 26 (01) :24-28

[2]

[Anonymous], 2010, MISHNEH TORAH SEFER, V12, P8

[3] STUDIES ON THE STEREOSPECIFICITY OF THE CLAVAMINIC ACID SYNTHASE CATALYZED HYDROXYLATION REACTION [J].

BALDWIN, JE ;

MERRITT, KD ;

SCHOFIELD, CJ ;

ELSON, SW ;

BAGGALEY, KH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (16) :1301-1302

[4] A SUBSTRATE-ANALOG STUDY ON CLAVAMINIC ACID SYNTHASE - POSSIBLE CLUES TO THE BIOSYNTHETIC ORIGIN OF PROCLAVAMIC ACID [J].

BALDWIN, JE ;

LLOYD, MD ;

WHASON, B ;

SCHOFIELD, CJ ;

ELSON, SW ;

BAGGALEY, KH ;

NICHOLSON, NH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (06) :500-502

[5]

BARTZ QR, 1951, AM REV TUBERC PULM, V63, P4

[6] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[7] STRUCTURE STEREOCHEMISTRY AND REACTIONS OF GUANIDINE MOIETY OF VIOMYCIN [J].

BYCROFT, BW ;

CROFT, LR ;

JOHNSON, AW ;

WEBB, T .

JOURNAL OF ANTIBIOTICS, 1969, 22 (03) :133-&

[8] TOTAL STRUCTURE OF CAPREOMYCIN IB, A TUBERCULOSTATIC PEPTIDE ANTIBIOTIC [J].

BYCROFT, BW ;

CAMERON, D ;

CROFT, LR ;

HASSANAL.A ;

JOHNSON, AW ;

WEBB, T .

NATURE, 1971, 231 (5301) :301-&

[9] Organocatalytic asymmetric assembly reactions:: One-pot synthesis of functionalized β-amino alcohols from aldehydes, ketones, and azodicarboxylates [J].

Chowdari, NS ;

Ramachary, DB ;

Barbas, CF .

ORGANIC LETTERS, 2003, 5 (10) :1685-1688

[10]

DYER JR, 1965, TETRAHEDRON LETT, P585

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