Issue 26, 2015
From the journal:

Organic & Biomolecular Chemistry

N–B dative bond-induced [3.3.0] bicyclic boronate-tethered exo-selective intramolecular Diels–Alder reaction†

Chao Feng,a   Hong Wang,a   Liang Xua  and  Pengfei Li*a  

* Corresponding authors

a Centre for Organic Chemistry, Frontier Institute of Science and Technology (FIST), Xi'an Jiaotong University, 99 Yanxiang Road, Xi'an, Shaanxi, China
E-mail: lipengfei@mail.xjtu.edu.cn

Abstract

We report herein a highly exo-selective intramolecular Diels–Alder reaction of alkenyl boronates which employs an N–B dative bond-involved bicyclic rigid tether. Complex C(sp3)-rich polycyclic molecules containing up to 8 stereocenters can be readily formed via an operationally simple two-step procedure.

Graphical abstract: N–B dative bond-induced [3.3.0] bicyclic boronate-tethered exo-selective intramolecular Diels–Alder reaction

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Article information

DOI
https://doi.org/10.1039/C5OB00917K
Article type
Communication
Submitted
06 May 2015
Accepted
20 May 2015
First published
20 May 2015

Org. Biomol. Chem., 2015,13, 7136-7139

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N–B dative bond-induced [3.3.0] bicyclic boronate-tethered exo-selective intramolecular Diels–Alder reaction

C. Feng, H. Wang, L. Xu and P. Li, Org. Biomol. Chem., 2015, 13, 7136 DOI: 10.1039/C5OB00917K

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