A Photochemical Route to 3-and 4-Hydroxy Derivatives of 2-Aminocyclobutane-1-carboxylic Acid with an all-cis Geometry

被引：22

作者：

Chang, Zong ^{[1
]}

Boyaud, France ^{[1
]}

Guillot, Regis ^{[2
]}

Boddaert, Thomas ^{[1
]}

Aitken, David J. ^{[1
]}

机构：

[1] Univ Paris Saclay, Univ Paris Sud, CNRS UMR 8182, ICMMO,Organ Synth Grp CP3A, 15 Rue Georges Clemenceau, F-91405 Orsay, France

[2] Univ Paris Saclay, Univ Paris Sud, CNRS UMR 8182, Serv Communs,ICMMO, 15 Rue Georges Clemenceau, F-91405 Orsay, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 01期

关键词：

BETA-AMINO-ACIDS; INTERMOLECULAR 2+2 PHOTOCYCLOADDITION; CYCLOBUTANE DERIVATIVES; ORGANIC-SYNTHESIS; ANALOGS; FOLDAMERS; PEPTIDES; ACCESS; FUNCTIONALIZATION; TRANSFORMATIONS;

D O I：

10.1021/acs.joc.7b02559

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Short grain-scale syntheses of both enantiomers of 2-amino-3-hydroxycyclobutane-1-carboxylic acid and of 2-amino-4-hydroxycyclobutanecarboxylic acid with an all-cis geometry are described. The sequences feature highly endo-selective [2 + 2]-photocycloaddition reactions followed by fully regioselective ring opening/Hofmann rearrangement/nitrogen protection, in a consecutive or one-pot protocol, followed by efficient resolution using a chiral oxazolidinone.

引用

页码：527 / 534

页数：8

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