TY  - JOUR
AB  - The stereodivergent synthesis of natural product frameworks via a single transformation using simple starting materials is a significant challenge. The prevalence of γ-butyrolactones in biologically active natural products has long motivated the development of enantioselective strategies towards their synthesis. Herein, we report an enantio- and diastereodivergent [3+2] annulation reaction for the synthesis of α,β-disubstituted γ-butyrolactones through cooperative N-heterocyclic carbene organocatalysis and iridium catalysis. This method overcomes the challenges of merging N-heterocyclic carbene organocatalysis with iridium catalysis by the appropriate choice of ligands. The use of two chiral catalysts allowed control over the relative and absolute configuration of the two formed stereocentres, thereby providing selective access to all four possible stereoisomers of the γ-lactone products. The transformation could be extended to the synthesis of δ-lactams via [4+2] annulation. The synthetic utility of this methodology was illustrated in the concise synthesis of the naturally occurring lignan (−)-hinokinin.
AU  - Singha, Santanu
AU  - Serrano, Eloisa
AU  - Mondal, Shobhan
AU  - Daniliuc, Constantin G.
AU  - Glorius, Frank
DA  - 2020
KW  - Asymmetric catalysis
KW  - Homogeneous catalysis
KW  - Synthetic chemistry methodology
KW  - Organocatalysis
LA  - eng
N1  - Supplementary information is available in the published version of the paper: https://doi.org/10.1038/s41929-019-0387-3
N1  - This document is the author’s final version of a published work that appeared in final form in Nature Catalysis (ISSN 2520-1158) after technical editing by the publisher. To access the final edited and published work, see https://doi.org/10.1038/s41929-019-0387-3
PY  - 2020
TI  - Diastereodivergent synthesis of enantioenriched α,β-disubstituted-γ-butyrolactones via cooperative N-heterocyclic carbene/Ir catalysis
UR  - https://nbn-resolving.org/urn:nbn:de:hbz:6-81169707953
Y2  - 2024-11-22T08:02:16
ER  -