Cu-Catalyzed Chemodivergent, Stereoselective Propargylic Dearomatization and Etherification of 2-Naphthols.Org Lett. 2021 08 20; 23(16):6262-6266.OL
Abstract
The first stereoselective propargylic dearomatization of 2-naphthol derivatives is reported using a chiral CuII-L10 complex. The reaction shows chemodivergent reactivity and produced propargyl dearomatization and etherification product for differently substituted 2-naphthols. Both the reactions generate the desired products in high yields with excellent chemo- and stereoselectivities (up to 99% ee, dr = 9:1) by using only 2 mol % catalyst loading. Dearomatization products contain a contiguous all-carbon quaternary-tertiary stereocenter and a terminal alkyne functionality.
Links
Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
34374540
Citation
Das, Braja Gopal, et al. "Cu-Catalyzed Chemodivergent, Stereoselective Propargylic Dearomatization and Etherification of 2-Naphthols." Organic Letters, vol. 23, no. 16, 2021, pp. 6262-6266.
Das BG, Shah S, Das A, et al. Cu-Catalyzed Chemodivergent, Stereoselective Propargylic Dearomatization and Etherification of 2-Naphthols. Org Lett. 2021;23(16):6262-6266.
Das, B. G., Shah, S., Das, A., & Singh, V. K. (2021). Cu-Catalyzed Chemodivergent, Stereoselective Propargylic Dearomatization and Etherification of 2-Naphthols. Organic Letters, 23(16), 6262-6266. https://doi.org/10.1021/acs.orglett.1c02027
Das BG, et al. Cu-Catalyzed Chemodivergent, Stereoselective Propargylic Dearomatization and Etherification of 2-Naphthols. Org Lett. 2021 08 20;23(16):6262-6266. PubMed PMID: 34374540.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Cu-Catalyzed Chemodivergent, Stereoselective Propargylic Dearomatization and Etherification of 2-Naphthols.
AU - Das,Braja Gopal,
AU - Shah,Sadhna,
AU - Das,Arko,
AU - Singh,Vinod K,
Y1 - 2021/08/10/
PY - 2021/8/11/pubmed
PY - 2021/8/11/medline
PY - 2021/8/10/entrez
SP - 6262
EP - 6266
JF - Organic letters
JO - Org Lett
VL - 23
IS - 16
N2 - The first stereoselective propargylic dearomatization of 2-naphthol derivatives is reported using a chiral CuII-L10 complex. The reaction shows chemodivergent reactivity and produced propargyl dearomatization and etherification product for differently substituted 2-naphthols. Both the reactions generate the desired products in high yields with excellent chemo- and stereoselectivities (up to 99% ee, dr = 9:1) by using only 2 mol % catalyst loading. Dearomatization products contain a contiguous all-carbon quaternary-tertiary stereocenter and a terminal alkyne functionality.
SN - 1523-7052
UR - https://www.unboundmedicine.com/medline/citation/34374540/Cu_Catalyzed_Chemodivergent_Stereoselective_Propargylic_Dearomatization_and_Etherification_of_2_Naphthols_
DB - PRIME
DP - Unbound Medicine
ER -
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