Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides.

Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides.
Angew Chem Int Ed Engl. 2018 Apr 19;:
Authors: Breit B, Steib P
Abstract
Herein, we report on the first enantioselective and atom-efficient, catalytic one-step dimerization methodology to selectively transform ω allenyl carboxylic acids into C2-symmetric, 14- to 28-membered bismacrolactones (macrodiolides). This convenient asymmetric access serves as an attractive route towards multiple naturally occuring homodimeric, macrocyclic scaffolds and demonstrates the excellent efficiency to construct the complex, symmetric core structures. Utilizing a rhodium catalyst with a modified chiral cyclopentylidene-diop ligand, the desired diolides were obtained in good to high yields, high diastereo- and excellent enantioselectivity.
PMID: 29673025 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - April 19, 2018 Category: Chemistry Authors: Breit B, Steib P Tags: Angew Chem Int Ed Engl Source Type: research