Subscribe to RSS
DOI: 10.1055/s-0040-1706471
Gram-Scale Robust Synthesis of 1-Chloro-2,3-dimethyl-4-phenylnaphthalene: A Promising Scaffold with Three Contiguous Reaction Positions
This research was partially supported by Grant-in-Aids for Scientific Research on Basic Areas (B) ‘18350056’, Priority Areas (A) ‘17035087’ and ‘18037068’, (C) 15K05508, and Exploratory Research ‘17655045’ from the Ministry of Education, Culture, Sports, Science and Technology (MEXT).
Abstract
A three-step reaction sequence for the gram-scale synthesis of 1-chloro-2,3-dimethyl-4-phenylnaphthalene was developed. (i) Stereoselective dichlorocarbene addition to methyl angelate afforded methyl (1S*,3S*)-2,2-dichloro-1,3-dimethylcyclopropane-1-carboxylate (78% yield, >98% purity, distillation). (ii) Addition reaction of two molar amounts of PhLi afforded (1S*,3S*)-2,2-dichloro-1,3-dimethylcyclopropyldiphenylmethanol (81% yield, >98% purity, recrystallization). (iii) Key SnCl4-mediated benzannulation produced the desired product (83% yield, >98% purity, recrystallization) with three contiguous reaction sites. Five derivatization examples including benzylic reactions and cross-couplings at the pendant Cl-position are demonstrated. Some relevant distinctive benzannulations are also discussed.
Key words
gem-dichrolocyclopropane - benzannulation - naphthalene - gram-scale - benzylic - cross-coupling partnersSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706471.
- Supporting Information
Publication History
Received: 22 July 2020
Accepted after revision: 14 August 2020
Article published online:
30 September 2020
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Döts KH. Angew. Chem. Int. Ed. 1975; 14: 644
- 1b Döts KH. Pure Appl. Chem. 1983; 55: 1689
- 1c Timko JM, Yamashita A. Org. Synth. 1993; 71: 72
- 2 Danheiser L, Brisbois RG, Kowalczyk JJ, Miller RF. J. Am. Chem. Soc. 1990; 112: 3093
- 3 Viswanathan GS, Wang M, Li C-J. Angew. Chem. Int. Ed. 2002; 41: 2138
- 4 Kabalka GW, Ju Y, Wu Z. J. Org. Chem. 2003; 68: 7915
- 5 Ilies L, Matsumoto A, Kobayashi M, Yoshikai N, Nakamura E. Synlett 2012; 23: 2381
- 6 Ponra S, Vitale MR, Michelet V, Ratovelomanana-Vital V. J. Org. Chem. 2015; 80: 3250
- 7 Recchi AM. S, Back DF, Zeni G. J. Org. Chem. 2017; 82: 2713
- 8a Fedorynski M. Chem. Rev. 2003; 103: 1099
- 8b Thankachan AP, Shndhu KS, Krishnan KK, Anilkumar G. Org. Biomol. Chem. 2015; 13: 8780
- 9 Sigma-Aldrich Catalogue No. 35934.
- 10a Seko S, Tanabe Y, Suzukamo G. Tetrahedron Lett. 1990; 31: 6883
- 10b Tanabe Y, Seko S, Nishii Y, Yoshida T, Utsumi N, Suzukamo G. J. Chem. Soc., Perkin Trans. 1 1996; 2157
- 11 Nishii Y, Yoshida T, Asano H, Wakasugi K, Morita J, Aso Y, Yoshida E, Motoyoshiya J, Aoyama H, Tanabe Y. J. Org. Chem. 2005; 70: 2667
- 12 Anderson KW, Ikawa T, Tundel RE, Buchwald SL. J. Am. Chem. Soc. 2006; 128: 10694
- 13 Wada K, Munakata K. Tetrahedron Lett. 1970; 2017
- 14 Lin T.-Y, Lo T.-B, Wang KT, Weinstein B. Tetrahedron Lett. 1967; 849
- 15a Newmann DJ, Cragg GM. J. Nat. Prod. 2007; 70: 461
- 15b Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2009; 48: 3224
- 15c Zhao C, Rakesh KP, Mumtaz S, Moku B, Asiri AM, Marwani HM, Manukumar HM, Qin H. RSC Adv. 2018; 8: 9487
- 16 Nishii Y, Wakasugi K, Koga K, Tanabe Y. J. Am. Chem. Soc. 2004; 126: 5358
- 17 Seko S. Japan Kokai Tokkyo Koho. 1994271484, 1994