Ni-Catalyzed Diastereoconvergent Intramolecular Alkene–Aldehyde Reductive Coupling: A Route to syn-Chromanols
Publication type: Journal Article
Publication date: 2024-04-26
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
38669085
Abstract
We demonstrate for the first time a nickel-catalyzed diastereoconvergent reductive coupling of a heteroatom-attached allyl moiety with aldehydes, viz., O-allyl, O-cinnamyl salicylaldehydes, and others, to afford syn-chromanols exclusively. The reaction proceeds through a [2 + 2 + 1] oxidative cycloaddition involving the active catalyst. This method is applicable to both terminal and internal olefin substrates. The formal syntheses of CP-199.330, CP-199.331, and CP-85.958 have been demonstrated. Control experiments, mass spectrometric analysis, and DFT studies supported the plausible mechanism and the origin of exclusive syn-selectivity.
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Ghosh S. et al. Ni-Catalyzed Diastereoconvergent Intramolecular Alkene–Aldehyde Reductive Coupling: A Route to syn-Chromanols // Organic Letters. 2024. Vol. 26. No. 18. pp. 4024-4029.
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Ghosh S., Rooj A., Chakrabortty R., Venkata Prasanth B. Ni-Catalyzed Diastereoconvergent Intramolecular Alkene–Aldehyde Reductive Coupling: A Route to syn-Chromanols // Organic Letters. 2024. Vol. 26. No. 18. pp. 4024-4029.
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TY - JOUR
DO - 10.1021/acs.orglett.4c01428
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c01428
TI - Ni-Catalyzed Diastereoconvergent Intramolecular Alkene–Aldehyde Reductive Coupling: A Route to syn-Chromanols
T2 - Organic Letters
AU - Ghosh, Sudipta
AU - Rooj, Arnab
AU - Chakrabortty, Rajesh
AU - Venkata Prasanth, B.
PY - 2024
DA - 2024/04/26
PB - American Chemical Society (ACS)
SP - 4024-4029
IS - 18
VL - 26
PMID - 38669085
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2024_Ghosh,
author = {Sudipta Ghosh and Arnab Rooj and Rajesh Chakrabortty and B. Venkata Prasanth},
title = {Ni-Catalyzed Diastereoconvergent Intramolecular Alkene–Aldehyde Reductive Coupling: A Route to syn-Chromanols},
journal = {Organic Letters},
year = {2024},
volume = {26},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c01428},
number = {18},
pages = {4024--4029},
doi = {10.1021/acs.orglett.4c01428}
}
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MLA
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Ghosh, Sudipta, et al. “Ni-Catalyzed Diastereoconvergent Intramolecular Alkene–Aldehyde Reductive Coupling: A Route to syn-Chromanols.” Organic Letters, vol. 26, no. 18, Apr. 2024, pp. 4024-4029. https://pubs.acs.org/doi/10.1021/acs.orglett.4c01428.