Literature DB >> 23903206

Recent advances in stereoselective bromofunctionalization of alkenes using N-bromoamide reagents.

Chong Kiat Tan1, Ying-Yeung Yeung.   

Abstract

Bromination reactions have been made a lot more convenient since the invention of N-bromoamide reagents. These reagents are more easily handled when compared to molecular bromine. In comparison to other halogens, brominating reagents sit in between chlorine and iodine on the reactivity scale, giving them an advantage in some cases. Recently, several important advances in enantioselective bromofunctionalization of alkenes using such reagents have been reported. This article will highlight the challenges and methods to surmount these problems. In addition, this article will also show the use of N-bromoamide reagents in expanding the scope of diastereoselective bromofunctionalization of alkenes. Examples include bromine initiated cyclic ether cascades and novel multicomponent reactions (MCRs).

Entities:  

Year:  2013        PMID: 23903206     DOI: 10.1039/c3cc43950j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  21 in total

1.  Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.

Authors:  Frederick J Seidl; Chang Min; Jovan A Lopez; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2018-11-12       Impact factor: 15.419

2.  Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis.

Authors:  Jeremy D Griffin; Cortney L Cavanaugh; David A Nicewicz
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-20       Impact factor: 15.336

3.  Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons.

Authors:  Brett N Hemric; Andy W Chen; Qiu Wang
Journal:  J Org Chem       Date:  2019-01-17       Impact factor: 4.354

4.  Synthesis of (+)-Disparlure via Enantioselective Iodolactonization.

Authors:  Daniel W Klosowski; Stephen F Martin
Journal:  Org Lett       Date:  2018-02-12       Impact factor: 6.005

Review 5.  Catalytic Enantioselective Dihalogenation in Total Synthesis.

Authors:  Matthew L Landry; Noah Z Burns
Journal:  Acc Chem Res       Date:  2018-04-17       Impact factor: 22.384

6.  Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement.

Authors:  Jeewani P Ariyarathna; Nur-E Alom; Leo P Roberts; Navdeep Kaur; Fan Wu; Wei Li
Journal:  J Org Chem       Date:  2022-02-10       Impact factor: 4.198

7.  A Mechanistically Inspired Halenium Ion Initiated Spiroketalization: Entry to Mono- and Dibromospiroketals.

Authors:  Kumar Dilip Ashtekar; Hadi Gholami; Mehdi Moemeni; Ankush Chakraborty; Lindsey Kiiskila; Xinliang Ding; Edmond Toma; Christopher Rahn; Babak Borhan
Journal:  Angew Chem Int Ed Engl       Date:  2022-01-11       Impact factor: 16.823

Review 8.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

Review 9.  Stereoselective Halogenation in Natural Product Synthesis.

Authors:  Won-jin Chung; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

10.  Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-06-23       Impact factor: 15.419

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