Organic Letters
Letter
Catalytic Asymmetric Pictet−Spengler-Type Reaction for the Syn-
thesis of Optically Active Indolo[3,4-cd][1]benzazepines. Org. Lett.
2011, 13, 5636−5639. (c) Li, P.; Huang, Y.; Hu, X.; Dong, X.-Q.;
Zhang, X. Access to Chiral Seven-Member Cyclic Amines via Rh-
Catalyzed Asymmetric Hydrogenation. Org. Lett. 2017, 19, 3855−
3858. (d) Liu, J.; Yang, X.; Zuo, Z.; Nan, J.; Wang, Y.; Luan, X.
Catalytic Enantioselective Tautomerization of Metastable Enamines.
Org. Lett. 2018, 20, 244−247. (e) Cheng, Q.; Xie, J.-H.; Weng, Y.-C.;
You, S.-L. Pd-Catalyzed Dearomatization of Anthranils with Vinyl-
cyclopropanes by [4 + 3] Cyclization Reaction. Angew. Chem., Int. Ed.
2019, 58, 5739−5743.
(3) (a) Kondo, K.; Kan, K.; Tanada, Y.; Bando, M.; Shinohara, T.;
Kurimura, M.; Ogawa, H.; Nakamura, S.; Hirano, T.; Yamamura, Y.;
Kido, M.; Mori, T.; Tominaga, M. Characterization of Orally Active
Nonpeptide Vasopressin V2 Receptor Agonist. Synthesis and
Biological Evaluation of Both the (5R)- and (5S)-Enantioisomers of
2-[1-(2-Chloro-4-pyrrolidin-1-yl-benzoyl)-2,3,4,5-tetrahydro-1H-1-
benzazepin-5-yl]-N-isopropylacetamide. J. Med. Chem. 2002, 45,
3805−3808. (b) Hou, F. F.; Zhang, X.; Zhang, G. H.; Xie, D.;
Chen, P. Y.; Zhang, W. R.; Jiang, J. P.; Liang, M.; Wang, G. B.; Liu, Z.
R.; Geng, R. W. Efficacy and Safety of Benazepril for Advanced
Chronic Renal Insufficiency. N. Engl. J. Med. 2006, 354, 131−140.
(c) Tashima, T.; Toriumi, Y.; Mochizuki, Y.; Nonomura, T.; Nagaoka,
S.; Furukawa, K.; Tsuru, H.; Adachi-Akahane, S.; Ohwada, T. Design,
Synthesis, and BK Channel-Opening Activity of Hexahydrodibenza-
zepinone Derivatives. Bioorg. Med. Chem. 2006, 14, 8014−8031.
(d) Kern, C.; Meyer, T.; Droux, S.; Schollmeyer, D.; Miculka, C.
Synthesis and Pharmacological Characterization of β2-Adrenergic
Agonist Enantiomers: Zilpaterol. J. Med. Chem. 2009, 52, 1773−1777.
(e) Wenzel, S. C.; Hoffmann, H.; Zhang, J.; Debussche, L.; Haag-
Richter, S.; Kurz, M.; Nardi, F.; Lukat, P.; Kochems, I.; Tietgen, H.;
Schummer, D.; Nicolas, J.-P.; Calvet, L.; Czepczor, V.; Vrignaud, P.;
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
Experimental procedures, characterization of products,
1
and copies of H and 13C NMR (PDF)
Accession Codes
CCDC 1936587 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This research was supported by National Research Foundation
o f K o r e a g r a n t s ( 2 0 1 9 R 1 A 2 C 2 0 0 5 7 0 6 a n d
2019R1A4A2001440), funded by the Korean government
(MEST). X-ray structural analysis was supported by “Human
Resources Program in Energy Technology”of the Korean
Institute of Energy Technology Evaluation and Planning
(KETEP), granted financial resource from the Ministry of
Trade, Industry, and Energy, Korea. (no. 20164030201380).
D.L. thanks the China Scholarship Council (no.
201508260066).
Muhlenweg, A.; Pelzer, S.; Muller, R.; Bronstrup, M. Production of
̈ ̈
̈
the Bengamide Class of Marine Natural Products in Myxobacteria:
Biosynthesis and Structure−Activity Relationships. Angew. Chem., Int.
Ed. 2015, 54, 15560−15564.
(4) Dolman, S. J.; Schrock, R. R.; Hoveyda, A. H. Enantioselective
Synthesis of Cyclic Secondary Amines through Mo-Catalyzed
Asymmetric Ring-Closing Metathesis (ARCM). Org. Lett. 2003, 5,
4899−4902.
(5) (a) Pellissier, H. Enantioselective Titanium-Promoted 1,2-
Additions of Carbon Nucleophiles to Carbonyl Compounds.
Tetrahedron 2015, 71, 2487−2524. (b) Kurono, N.; Ohkuma, T.
Catalytic Asymmetric Cyanation Reactions. ACS Catal. 2016, 6, 989−
REFERENCES
■
(1) (a) Zhang, A.; Neumeyer, J. L.; Baldessarini, R. J. Recent
Progress in Development of Dopamine Receptor Subtype-Selective
Agents: Potential Therapeutics for Neurological and Psychiatric
Disorders. Chem. Rev. 2007, 107, 274−302. (b) Rouden, J.; Lasne,
M.-C.; Blanchet, J.; Baudoux, J. (−)-Cytisine and Derivatives:
Synthesis, Reactivity, and Applications. Chem. Rev. 2014, 114, 712−
778. (c) Wu, W.-L.; Burnett, D. A.; Spring, R.; Greenlee, W. J.; Smith,
M.; Favreau, L.; Fawzi, A.; Zhang, H.; Lachowicz, J. E. Dopamine D1/
D5 Receptor Antagonists with Improved Pharmacokinetics: Design,
Synthesis, and Biological Evaluation of Phenol Bioisosteric Analogues
of Benzazepine D1/D5 Antagonists. J. Med. Chem. 2005, 48, 680−693.
(d) Novoa, A.; Van Dorpe, S.; Wynendaele, E.; Spetea, M.; Bracke,
N.; Stalmans, S.; Betti, C.; Chung, N. N.; Lemieux, C.; Zuegg, J.;
́
1023. (c) Diner, C.; Szabo, K. J. Recent Advances in the Preparation
and Application of Allylboron Species in Organic Synthesis. J. Am.
Chem. Soc. 2017, 139, 2−14. (d) Wu, H.-L.; Chang, C.-A.; Wu, P.-Y.;
Uang, B.-J. Recent Developments in Zn-Catalyzed Asymmetric
Addition Reaction to Ketones: Syntheses of Chiral Tertiary Alcohols.
Tetrahedron Lett. 2017, 58, 706−710. (e) Quan, M.; Wu, L.; Yang, G.;
Zhang, W. Pd(II), Ni(II) and Co(II)-Catalyzed Enantioselective
Additions of Organoboron Reagents to Ketimines. Chem. Commun.
2018, 54, 10394−10404. (f) Riant, O.; Hannedouche, J. Asymmetric
Catalysis for the Construction of Quaternary Carbon Centres:
Nucleophilic Addition on Ketones and ketimines. Org. Biomol.
Chem. 2007, 5, 873−888. (g) Hatano, M.; Ishihara, K. Recent
Progress in the Catalytic Synthesis of Tertiary Alcohols from Ketones
with Organometallic Reagents. Synthesis 2008, 2008, 1647−1675.
(h) Kumagai, N.; Shibasaki, M. Recent Advances in Catalytic
Asymmetric C−C Bond-Forming Reactions to Ketimines Promoted
by Metal-Based Catalysts. Bull. Chem. Soc. Jpn. 2015, 88, 503−517.
́
Cooper, M. A.; Tourwe, D.; De Spiegeleer, B.; Schiller, P. W.; Ballet,
S. Variation of the Net Charge, Lipophilicity, and Side Chain
Flexibility in Dmt1-DALDA: Effect on Opioid Activity and
Biodistribution. J. Med. Chem. 2012, 55, 9549−9561. (e) Tewes, B.;
Frehland, B.; Schepmann, D.; Robaa, D.; Uengwetwanit, T.; Gaube,
̀
́
(i) Collados, J. F.; Sola, R.; Harutyunyan, S. R.; Macia, B. Catalytic
Synthesis of Enantiopure Chiral Alcohols via Addition of Grignard
Reagents to Carbonyl Compounds. ACS Catal. 2016, 6, 1952−1970.
(j) Bisai, V.; Singh, V. K. Recent Developments in Asymmetric
Alkynylations. Tetrahedron Lett. 2016, 57, 4771−4784. (k) Liu, Y.-L.;
Lin, X.-T. Recent Advances in Catalytic Asymmetric Synthesis of
Tertiary Alcohols via Nucleophilic Addition to Ketones. Adv. Synth.
Catal. 2019, 361, 876−918.
F.; Winckler, T.; Sippl, W.; Wunsch, B. Enantiomerically Pure 2-
̈
Methyltetrahydro-3-benzazepin-1-ols Selectively Blocking GluN2B
Subunit Containing N-Methyl-D-aspartate Receptors. J. Med. Chem.
2015, 58, 6293−6305.
(2) (a) He, H.; Liu, W.-B.; Dai, L.-X.; You, S.-L. Enantioselective
Synthesis of 2,3-Dihydro-1H-benzo[b]azepines: Iridium-Catalyzed
Tandem Allylic Vinylation/Amination Reaction. Angew. Chem., Int.
Ed. 2010, 49, 1496−1499. (b) Cheng, D.-J.; Wu, H.-B.; Tian, S.-K.
D
Org. Lett. XXXX, XXX, XXX−XXX