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Literature DB >> 28718214

A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

Xun Liu¹, T Maxwell Deaton¹, Fredrik Haeffner¹, James P Morken¹.

Abstract

We describe an unusual net [2+2] cycloaddition reaction between boron alkylidenes and unactivated alkenes. This reaction provides a new method for the construction of carbocyclic ring systems bearing versatile organoboronic esters. Aside from surveying the scope of this reaction, we provide details about the mechanistic underpinnings of this process, and examine its application to the synthesis of the natural product aphanamal.

Entities: Chemical Disease Gene Species

Keywords: alkenes; boron; cyclization; reaction mechanisms; total synthesis

Mesh：

Substances：
Alkenes
Alkynes
Boron

Year: 2017 PMID： 28718214 PMCID： PMC5699471 DOI： 10.1002/anie.201705720

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

48 in total

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Journal: Org Lett Date: 2000-07-27 Impact factor: 6.005

2. Synthesis of cyclopentitols by ring-closing approaches.

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3. Copper(I)-catalyzed boryl substitution of unactivated alkyl halides.

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4. Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes.

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5. Cobalt-Catalyzed Benzylic Borylation: Enabling Polyborylation and Functionalization of Remote, Unactivated C(sp(3))-H Bonds.

Authors: W Neil Palmer; Jennifer V Obligacion; Iraklis Pappas; Paul J Chirik
Journal: J Am Chem Soc Date: 2016-01-12 Impact factor: 15.419

6. Optimization of Reaction and Substrate Activation in the Stereoselective Cross-Coupling of Chiral 3,3-Diboronyl Amides.

Authors: Jack Chang Hung Lee; Ho-Yan Sun; Dennis G Hall
Journal: J Org Chem Date: 2015-07-01 Impact factor: 4.354

7. Pd(0)-Catalyzed Cross-Coupling of 1,1-Diboronates with 2,2'-Dibromobiphenyls: Synthesis of 9H-Fluorenes.

Authors: Shuai Xu; Xianghang Shangguan; Huan Li; Yan Zhang; Jianbo Wang
Journal: J Org Chem Date: 2015-07-16 Impact factor: 4.354

8. Copper-catalyzed cross-coupling reactions of epoxides with gem-diborylmethane: access to γ-hydroxyl boronic esters.

Authors: Ahmed Ebrahim-Alkhalil; Zhen-Qi Zhang; Tian-Jun Gong; Wei Su; Xiao-Yu Lu; Bin Xiao; Yao Fu
Journal: Chem Commun (Camb) Date: 2016-03-14 Impact factor: 6.222

9. Synthesis of Enantioenriched Alkylfluorides by the Fluorination of Boronate Complexes.

Authors: Christopher Sandford; Ramesh Rasappan; Varinder K Aggarwal
Journal: J Am Chem Soc Date: 2015-08-05 Impact factor: 15.419

10. A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms.

Authors: Steven J Ferrara; Jonathan W Burton
Journal: Chemistry Date: 2016-07-08 Impact factor: 5.236

6 in total

1. Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.

Authors: Michael Z Liang; Simon J Meek
Journal: J Am Chem Soc Date: 2020-05-18 Impact factor: 15.419