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

共 50 条

[1] Stereoselective synthesis of an all-cis 1,2,3-trisubstituted cyclopropane carboxylic acid
Kiau, Susanne
Gonzales-Bobes, Francisco
Fenster, Michael D. B.
Kolotuchin, Sergei
Kolla, Laxma
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[2] On the stability of clusters containing all-cis 1,2,3,4,5,6-hexafluorocyclohexane
McDowell, Sean A. C.
COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2017, 1108 : 18 - 22
[3] All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexane
Keddie, Neil S.
Slawin, Alexandra M. Z.
Lebl, Tomas
Philp, Douglas
O'Hagan, David
NATURE CHEMISTRY, 2015, 7 (06) : 483 - 488
[4] All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexane
Keddie N.S.
Slawin A.M.Z.
Lebl T.
Philp D.
O'Hagan D.
Nature Chemistry, 2015, 7 (6) : 483 - 488
[5] A Convenient Synthetic Route to Derivatives of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylic Acid
Khlebnikov, A. F.
Nikiforova, T. Y.
Novikov, M. S.
Kostikov, R. R.
Synthesis, (06):
[6] A convenient synthetic route to derivatives of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
Khlebnikov, AF
Nikiforova, TY
Novikov, MS
Kostikov, RR
SYNTHESIS-STUTTGART, 1997, (06): : 677 - &
[7] A computational study of simultaneous cation/anion interactions in model clusters containing all-cis 1,2,3-trifluorocyclopropane (F3C3H3) and all-cis 1,2,3,4-tetrafluorobutane (F4C4H4)
McDowell, Sean A. C.
CHEMICAL PHYSICS LETTERS, 2016, 665 : 105 - 110
[8] Hydroxylated pyrrolidines.: Enantiospecific synthesis of all-cis 2,3,4,5-substituted pyrrolidine derivatives from serine
Verma, SK
Atanes, MN
Busto, JH
Thai, DL
Rapoport, H
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04): : 1314 - 1318
[9] Cultured fish cells metabolize octadecapentaenoic acid (all-cis Δ3,6,9,12,15-18:5) to octadecatetraenoic acid (all-cis Δ6,9,12,15-18:4) via its 2-trans intermediate (trans Δ2, all-cis Δ6,9,12,15-18:5)
Ghioni, C
Porter, AEA
Sadler, IH
Tocher, DR
Sargent, JR
LIPIDS, 2001, 36 (02) : 145 - 152
[10] Vibrational circular dichroism as a probe of solid-state organisation of derivatives of cyclic β-amino acids: Cis- and trans-2-aminocyclobutane-1-carboxylic acid
Declerck, Valerie
Perez-Mellor, Ariel
Guillot, Regis
Aitken, David J.
Mons, Michel
Zehnacker, Anne
CHIRALITY, 2019, 31 (08) : 547 - 560

← 1 2 3 4 5 →