Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process-Reference-Cited by-同舟云学术

Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process

Published:2023-11-23 Issue: Volume: Page:
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Jarava‐Barrera Carlos¹,Parra Alejandro¹,Quesada Sergio¹,Orgaz‐Gordillo Sergio¹,Fernández de la Pradilla Roberto²,Viso Alma²^ORCID,Teresa Javier¹,Alonso Inés¹³,Tortosa Mariola¹³^ORCID

Affiliation:

1. Organic Chemistry Department Center for Innovation in Advanced Chemistry (ORFEO-CINQA) Universidad Autónoma de Madrid (UAM) 28049 Madrid Spain

2. Instituto de Química Orgánica General (IQOG) CSIC Juan de la Cierva 3 28006 Madrid Spain

3. Institute for Advanced Research in Chemical Sciences (IAdChem) Universidad Autónoma de Madrid (UAM) 28049 Madrid Spain

Abstract

AbstractAn array of enantioenriched vinyl boronates bearing an allylic carbonate moiety have been prepared through selective hydroboration of propargyl carbonates. Treatment of these vinyl boronates with TBAF in THF affords enantioenriched 1,3‐disubstituted allenes through a novel 1,2‐anti elimination in good yields and high enantiospecificities.

Funder

Ministerio de Ciencia e Innovación

Publisher

Wiley

Subject

General Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202300813

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5. Allenes in Molecular Materials