Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.
Publication
, Journal Article
Onyeagusi, CI; Shao, X; Malcolmson, SJ
Published in: Organic letters
February 2020
We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic α-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo γ-selective alkylation with a Pd-DTBM-SEGPHOS catalyst, which additionally promotes regioselective addition to the diene and delivers products in up to 86% yield, 10:1 dr, and 97.5:2.5 er.
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Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
February 2020
Volume
22
Issue
4
Start / End Page
1681 / 1685
Related Subject Headings
- Stereoisomerism
- Palladium
- Organic Chemistry
- Molecular Structure
- Coordination Complexes
- Catalysis
- Amines
- Alkylation
- Alkadienes
- 34 Chemical sciences
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ICMJE
MLA
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Onyeagusi, C. I., Shao, X., & Malcolmson, S. J. (2020). Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes. Organic Letters, 22(4), 1681–1685. https://doi.org/10.1021/acs.orglett.0c00342
Onyeagusi, Chibueze I., Xinxin Shao, and Steven J. Malcolmson. “Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.” Organic Letters 22, no. 4 (February 2020): 1681–85. https://doi.org/10.1021/acs.orglett.0c00342.
Onyeagusi CI, Shao X, Malcolmson SJ. Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes. Organic letters. 2020 Feb;22(4):1681–5.
Onyeagusi, Chibueze I., et al. “Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.” Organic Letters, vol. 22, no. 4, Feb. 2020, pp. 1681–85. Epmc, doi:10.1021/acs.orglett.0c00342.
Onyeagusi CI, Shao X, Malcolmson SJ. Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes. Organic letters. 2020 Feb;22(4):1681–1685.
Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
February 2020
Volume
22
Issue
4
Start / End Page
1681 / 1685
Related Subject Headings
- Stereoisomerism
- Palladium
- Organic Chemistry
- Molecular Structure
- Coordination Complexes
- Catalysis
- Amines
- Alkylation
- Alkadienes
- 34 Chemical sciences