Literature DB >> 27709816

Stereocontrolled Syntheses of Seven-Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction.

Nels C Gerstner1, Christopher S Adams1, Maik Tretbar1, Jennifer M Schomaker2.   

Abstract

A tandem allene aziridination/[4+3]/reduction sequence converts simple homoallenic sulfamates into densely functionalized aminated cycloheptenes, where the relative stereochemistry at five contiguous asymmetric centers can be controlled through the choice of the solvent and the reductant. The products resulting from this chemistry can be readily transformed into complex molecular scaffolds which contain up to seven contiguous stereocenters.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allenes; cycloaddition; heterocycles; rhodium; synthetic methods

Mesh：

Substances：

Year:  2016        PMID： 27709816      PMCID： PMC5218842          DOI： 10.1002/anie.201606195

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  23 in total

1.  Diastereocontrol of [4 + 3] Cyclic Oxyallyl Cycloadditions by Alkoxy Substituents.

Authors:  Sung Yun Cho; Jae Chol Lee; Jin Kun Cha
Journal:  J Org Chem       Date:  1999-05-14       Impact factor: 4.354

2.  Intramolecular 4 + 3 cycloadditions. Aspects of stereocontrol in the synthesis of cyclooctanoids. A synthesis of (+)-dactylol.

Authors:  M Harmata; P Rashatasakhon
Journal:  Org Lett       Date:  2000-09-07       Impact factor: 6.005

3.  8-Oxabicyclo[3.2.1]oct-6-en-3-ones: application to the asymmetric synthesis of polyoxygenated building blocks.

Authors:  Ingo V Hartung; H Martin R Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-02       Impact factor: 15.336

4.  A Lewis acid catalyzed intramolecular [4+3] cycloaddition route to polycyclic systems that contain a seven-membered ring.

Authors:  Gildas Prié; Natacha Prévost; Heather Twin; Stephanie A Fernandes; Jerome F Hayes; Michael Shipman
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-03       Impact factor: 15.336

5.  The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings.

Authors:  Merle A Battiste; Phillip M Pelphrey; Dennis L Wright
Journal:  Chemistry       Date:  2006-04-24       Impact factor: 5.236

6.  The first epoxidations of 1-amidoallenes. A general entry to nitrogen-substituted oxyallyl cations in highly stereoselective [4 +3] cycloadditions.

Authors:  H Xiong; R P Hsung; C R Berry; C Rameshkumar
Journal:  J Am Chem Soc       Date:  2001-07-25       Impact factor: 15.419

Review 7.  Exploration of fundamental and synthetic aspects of the intramolecular 4 + 3 cycloaddition reaction.

Authors:  M Harmata
Journal:  Acc Chem Res       Date:  2001-07       Impact factor: 22.384

8.  Chiral Lewis acid-catalyzed highly enantioselective [4 + 3] cycloaddition reactions of nitrogen-stabilized oxyallyl cations derived from allenamides.

Authors:  Jian Huang; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

9.  Cyclic sulfamidates as vehicles for the synthesis of substituted lactams.

Authors:  John F Bower; Jakub Svenda; Andrew J Williams; Jonathan P H Charmant; Ron M Lawrence; Peter Szeto; Timothy Gallagher
Journal:  Org Lett       Date:  2004-12-09       Impact factor: 6.005

10.  Intramolecular PhI=O mediated copper-catalyzed aziridination of unsaturated sulfamates: a new direct access to polysubstituted amines from simple homoallylic alcohols.

Authors:  Fernando Duran; Loïc Leman; Alberto Ghini; Gerardo Burton; Philippe Dauban; Robert H Dodd
Journal:  Org Lett       Date:  2002-07-25       Impact factor: 6.005
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  8 in total

1.  Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles.

Authors:  Mirza A Saputra; Binod Nepal; Nitin S Dange; Pu Du; Frank R Fronczek; Revati Kumar; Rendy Kartika
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-23       Impact factor: 15.336

2.  Biomimetic 2-Imino-Nazarov Cyclizations via Eneallene Aziridination.

Authors:  Joshua R Corbin; Devin R Ketelboeter; Israel Fernández; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2020-03-10       Impact factor: 15.419

3.  Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.

Authors:  Hillary J Dequina; Jennifer M Schomaker
Journal:  Trends Chem       Date:  2020-09-02

4.  Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes.

Authors:  Logan A Combee; Shea L Johnson; Julie E Laudenschlager; Michael K Hilinski
Journal:  Org Lett       Date:  2019-03-25       Impact factor: 6.005

5.  Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

Authors:  Yidong Wang; Sarah G Scrivener; Xiao-Dong Zuo; Ruihan Wang; Philip N Palermo; Ethan Murphy; Austin C Durham; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2021-09-07       Impact factor: 16.383

6.  Ring Expansion of Bicyclic Methyleneaziridines via Concerted, Near-Barrierless [2,3]-Stevens Rearrangements of Aziridinium Ylides.

Authors:  Steven C Schmid; Ilia A Guzei; Israel Fernández; Jennifer M Schomaker
Journal:  ACS Catal       Date:  2018-07-17       Impact factor: 13.084

Review 7.  Synthesis and applications of methyleneaziridines.

Authors:  Bin Pan; Feng Li; Yingying Zhao
Journal:  RSC Adv       Date:  2020-10-27       Impact factor: 4.036

8.  Intermolecular [3+3] ring expansion of aziridines to dehydropiperi-dines through the intermediacy of aziridinium ylides.

Authors:  Josephine Eshon; Kate A Nicastri; Steven C Schmid; William T Raskopf; Ilia A Guzei; Israel Fernández; Jennifer M Schomaker
Journal:  Nat Commun       Date:  2020-03-09       Impact factor: 14.919
  8 in total

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