Amine-tethered phenylboronic acid-enabling ring-opening strategy for carbon chain elongation from double aldol cyclic hemiacetals

The addition of carbon nucleophiles to cyclic hemiacetal forms of double aldols is a promising approach toward the synthesis of structurally attractive 1,3-polyol derivatives. Cyclic hemiacetals are generally unreactive to carbon nucleophiles under neutral conditions, however, because the electrophi...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-07, Vol.17 (27), p.6562-6565
Main Authors: Kanzaki, Yamato, Hirao, Yuki, Mitsunuma, Harunobu, Kanai, Motomu
Format: Article
Language:English
Subjects:
Acids
Aldehydes
Carbon
Carbon cycle
Elongation
Nucleophiles
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The addition of carbon nucleophiles to cyclic hemiacetal forms of double aldols is a promising approach toward the synthesis of structurally attractive 1,3-polyol derivatives. Cyclic hemiacetals are generally unreactive to carbon nucleophiles under neutral conditions, however, because the electrophilic aldehyde function is masked. Here we developed an amine-tethered phenylboronic acid 7g , which transforms double aldol cyclic hemiacetals to ring-opened linear aldehydes. Combined with the previously-developed copper-catalysed asymmetric double aldol reaction (L. Lin, K. Yamamoto, H. Mitsunuma, Y. Kanzaki, S. Matsunaga and M. Kanai, J. Am. Chem. Soc. , 2015, 137 , 15418), this method produced synthetically useful chiral building blocks containing a 1,3-di- or tri-ol moiety. A boron reagent for the ring-opening reaction of double aldol cyclic hemiacetals to generate their aldehyde forms is developed.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01263j