Asymmetric Reduction of Lactam-Based β-Aminoacrylates. Synthesis of Heterocyclic β2-Amino Acids

被引：19

作者：

Campello, Hugo Rego ^{[1
]}

Parker, Jeremy ^{[2
]}

Perry, Matthew ^{[3
]}

Ryberg, Per ^{[4
,5
]}

Gallagher, Timothy ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Cantocks Close, Bristol BS8 1TS, Avon, England

[2] AstraZeneca, Pharmaceut Dev, Silk Rd,Business Pk, Macclesfield SK10 2NA, Cheshire, England

[3] AstraZeneca R&D, Innovat Med, R&I Chem, AstraZeneca, SE-43183 Molndal, Sweden

[4] AstraZeneca, PR&D Sodertalje, S-15185 Sodertalje, Sweden

[5] Ferring Pharmaceut, Kay Fiskers Pl 11, DK-2300 Copenhagen S, Denmark

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 16期

关键词：

UNSATURATED CARBOXYLIC-ACIDS; ENANTIOSELECTIVE SYNTHESIS; CATALYZED HYDROGENATION; DERIVATIVES; ALKALOIDS; LIGANDS; COMPLEXES; CYTISINE; NITRONES; ESTERS;

D O I：

10.1021/acs.orglett.6b02074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ability to affect asymmetric reduction of heterocyclic beta-aminoacrylates 1 (n = 1-3) hag been assessed with pyrrolidine and piperidone variants generating the corresponding N-heterocyclic beta(2)-amino acids 3b and 5b with high enantioselectivity (>= 97% ee) using a Rh/WALPHOS catalyst combination. The use of the carboxylic acid substrate was essential; the corresponding esters do undergo reduction but led to racemic products. The seven-ring azepanone variant (as the carboxylic acid 9b) underwent reduction, but only a minimal level of asymmetric induction was observed.

引用

页码：4124 / 4127

页数：4

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