Rhodium-Catalyzed Asymmetric Allylic Dearomatization of β-Naphthols: Enantioselective Control of Prochiral Nucleophiles.Org Lett. 2019 08 02; 21(15):6130-6134.OL
Abstract
A highly enantioselective rhodium-catalyzed allylic dearomatization of β-naphthols with racemic aryl vinyl carbinol is described. In the presence of a Rh-catalyst derived from [Rh(C2H4)Cl]2 and chiral (P, olefin)-ligand with TFA as an additive, the functionalized β-naphthalenone compounds bearing an all-carbon-substituted quaternary stereogenic center were obtained in good yields with excellent enantioselectivity. In addition, this protocol features the enantioselective control of prochiral nucleophiles and provides the first illustration of Rh-catalyzed asymmetric allylic dearomatization.
Links
Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
31318562
Citation
Tang, Sheng-Biao, et al. "Rhodium-Catalyzed Asymmetric Allylic Dearomatization of β-Naphthols: Enantioselective Control of Prochiral Nucleophiles." Organic Letters, vol. 21, no. 15, 2019, pp. 6130-6134.
Tang SB, Tu HF, Zhang X, et al. Rhodium-Catalyzed Asymmetric Allylic Dearomatization of β-Naphthols: Enantioselective Control of Prochiral Nucleophiles. Org Lett. 2019;21(15):6130-6134.
Tang, S. B., Tu, H. F., Zhang, X., & You, S. L. (2019). Rhodium-Catalyzed Asymmetric Allylic Dearomatization of β-Naphthols: Enantioselective Control of Prochiral Nucleophiles. Organic Letters, 21(15), 6130-6134. https://doi.org/10.1021/acs.orglett.9b02285
Tang SB, et al. Rhodium-Catalyzed Asymmetric Allylic Dearomatization of β-Naphthols: Enantioselective Control of Prochiral Nucleophiles. Org Lett. 2019 08 2;21(15):6130-6134. PubMed PMID: 31318562.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Rhodium-Catalyzed Asymmetric Allylic Dearomatization of β-Naphthols: Enantioselective Control of Prochiral Nucleophiles.
AU - Tang,Sheng-Biao,
AU - Tu,Hang-Fei,
AU - Zhang,Xiao,
AU - You,Shu-Li,
Y1 - 2019/07/18/
PY - 2019/7/19/pubmed
PY - 2019/7/19/medline
PY - 2019/7/19/entrez
SP - 6130
EP - 6134
JF - Organic letters
JO - Org Lett
VL - 21
IS - 15
N2 - A highly enantioselective rhodium-catalyzed allylic dearomatization of β-naphthols with racemic aryl vinyl carbinol is described. In the presence of a Rh-catalyst derived from [Rh(C2H4)Cl]2 and chiral (P, olefin)-ligand with TFA as an additive, the functionalized β-naphthalenone compounds bearing an all-carbon-substituted quaternary stereogenic center were obtained in good yields with excellent enantioselectivity. In addition, this protocol features the enantioselective control of prochiral nucleophiles and provides the first illustration of Rh-catalyzed asymmetric allylic dearomatization.
SN - 1523-7052
UR - https://www.unboundmedicine.com/medline/citation/31318562/Rhodium_Catalyzed_Asymmetric_Allylic_Dearomatization_of_β_Naphthols:_Enantioselective_Control_of_Prochiral_Nucleophiles_
DB - PRIME
DP - Unbound Medicine
ER -
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