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Synlett 2017; 28(18): 2453-2459
DOI: 10.1055/s-0036-1588488
DOI: 10.1055/s-0036-1588488
cluster
(HMe2SiCH2)2: A Useful Reagent for B(C6F5)3-Catalyzed Reduction–Lactonization of Keto Acids: Concise Syntheses of (–)-cis-Whisky and (–)-cis-Cognac Lactones
Authors
We are grateful for financial support from the National Natural Science Foundation of China (21290180, 21622202, 21502125).
Weitere Informationen
Publikationsverlauf
Received: 23. April 2017
Accepted after revision: 10. Juni 2017
Publikationsdatum:
19. Juli 2017 (online)
Published as part of the Cluster Silicon in Synthesis and Catalysis
Abstract
(HMe2SiCH2)2 has been utilized as a useful reagent for B(C6F5)3-catalyzed reduction–lactonization of keto acids to synthesize γ- and δ-lactones. The process led concisely to (–)-cis-whisky and (–)-cis-cognac lactones in respective overall yields of 32% and 36%.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588488.
- Supporting Information (PDF)
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References and Notes
- 1a Alonso DM. Wettstein SG. Dumesic JA. Green Chem. 2013; 15: 584
- 1b Lorente A. Merketegi JL. Albericio F. Álvarez M. Chem. Rev. 2013; 113: 4567
- 2a Kitson RR. A. Millemaggi A. Taylor RJ. K. Angew. Chem. Int. Ed. 2009; 48: 9426
- 2b Salvador G. Margarita P. Pablo R. Jose S. Mini-Rev. Org. Chem. 2009; 6: 345
- 3a Fábos V. Mika LT. Horváth IT. Organometallics 2014; 33: 181
- 3b Shimizu K.-I. Kanno S. Kon K. Green Chem. 2014; 16: 3899
- 3c Yang Z. Huang Y.-B. Guo Q.-X. Fu Y. Chem. Commun. 2013; 49: 5328
- 4a Ramachandran PV. Pitre S. Brown HC. J. Org. Chem. 2002; 67: 5315
- 4b Frenette R. Kakushima M. Zamboni R. Young RN. Verhoeven TR. J. Org. Chem. 1987; 52: 304
- 5a Nikolaos D. Erhan O. Bill M. Synlett 2016; 27: 1760
- 5b Oestreich M. Hermeke J. Mohr J. Chem. Soc. Rev. 2015; 44: 2202
- 5c Robert T. Oestreich M. Angew. Chem. Int. Ed. 2013; 52: 5216
- 5d Hatano M. Ishihara K. Chem. Commun. 2012; 48: 4273
- 5e Erker G. Chem. Commun. 2003; 13: 1469
- 5f Chen EY.-X. Marks TJ. Chem. Rev. 2000; 100: 1391
- 5g Ishihara K. Yamamoto H. Eur. J. Org. Chem. 1999; 527
- 5h Piers WE. Chivers T. Chem. Soc. Rev. 1997; 26: 345
- 5i Massey AG. Park AJ. Stone FG. A. Proc. Chem. Soc. 1963; 212
- 5j Yang X. Stern CL. Marks TJ. J. Am. Chem. Soc. 1991; 113: 3623
- 5k Ishihara K. Hananki N. Yamamoto H. Synlett 1993; 577
- 5l Ishihara K. Hananki N. Yamamoto H. Synlett 1995; 721
- 5m Temme B. Erker G. Karl J. Luftmann H. Fröhlich R. Kotila S. Angew. Chem., Int. Ed. Engl. 1995; 34: 1755
- 5n Parks DJ. Piers WE. J. Am. Chem. Soc. 1996; 118: 9440
- 5o Welch GC. Juan RR. S. Masuda JD. Stephan DW. Science 2006; 314: 1124
- 5p Spies P. Erker G. Kehr G. Bergander K. Fröhlich R. Grimme S. Stephan DW. Chem. Commun. 2007; 5072
- 6a Houghton AY. Hurmalainen J. Mansikkamäki A. Piers WE. Tuononen HM. Nat. Chem. 2014; 6: 983
- 6b Hermeke J. Mewald M. Oestreich M. J. Am. Chem. Soc. 2013; 135: 17537
- 6c Sakata K. Fujimoto H. J. Org. Chem. 2013; 78: 12505
- 6d Piers WE. Marwitz AJ. V. Mercier LG. Inorg. Chem. 2011; 50: 12252
- 6e Rendler S. Oestreich M. Angew. Chem. Int. Ed. 2008; 47: 5997
- 6f Parks DJ. Blackwell JM. Piers WE. J. Org. Chem. 2000; 65: 3090
- 7a Kim YC. Chang S. Angew. Chem. Int. Ed. 2016; 55: 218
- 7b Ma YH. Wang BL. Zhang L. Hou ZM. J. Am. Chem. Soc. 2016; 138: 3663
- 7c Wübbolt S. Oestreich M. Angew. Chem. Int. Ed. 2015; 54: 15876
- 7d Kim DW. Joung S. Kim JG. Chang S. Angew. Chem. Int. Ed. 2015; 54: 14805
- 7e Chatterjee I. Oestreich M. Angew. Chem. Int. Ed. 2015; 54: 1965
- 7f Gandhamsetty N. Park S. Chang S. J. Am. Chem. Soc. 2015; 137: 15176
- 7g Zhang Z. Du H. Angew. Chem. Int. Ed. 2015; 54: 623
- 7h Gandhamsetty N. Joung S. Park S.-W. Park S. Chang S. J. Am. Chem. Soc. 2014; 136: 16780
- 7i Liu Y. Du H. J. Am. Chem. Soc. 2013; 135: 6810
- 7j Bézier D. Park S. Brookhart M. Org. Lett. 2013; 15: 496
- 7k Mewald M. Oestreich M. Chem. Eur. J. 2012; 18: 14079
- 7l Geier SJ. Chase PA. Stephan DW. Chem. Commun. 2010; 46: 4884
- 7m Shchepin R. Xu C. Dussault P. Org. Lett. 2010; 12: 4772
- 7n Harrison DJ. McDonald R. Rosenberg L. Organometallics 2005; 24: 1398
- 7o Chandrasekhar S. Reddy CR. Babu BN. J. Org. Chem. 2002; 67: 9080
- 7p Rubin M. Schwier T. Gevorgyan V. J. Org. Chem. 2002; 67: 1936
- 7q Blackwell JM. Morrison DJ. Piers WE. Tetrahedron 2002; 58: 8247
- 7r Blackwell JM. Sonmor ER. Scoccitti T. Piers WE. Org. Lett. 2000; 2: 3921
- 8a Hazra CK. Gandhamsetty N. Park S. Chang S. Nat. Commun. 2016; 7: 13431
- 8b Bender TA. Dabrowski JA. Zhong HY. Gagne MR. Org. Lett. 2016; 18: 4120
- 8c Adduci LL. Bender TA. Dabrowski JA. Gagné MR. Nat. Chem. 2015; 7: 576
- 8d Drosos N. Morandi B. Angew. Chem. Int. Ed. 2015; 54: 8814
- 8e Mack DJ. Guo B. Njardarson JT. Chem. Commun. 2012; 48: 7844
- 8f Chojnowski J. Rubinsztajn S. Cella JA. Fortuniak W. Cypryk M. Kurjata J. Kaźmierski K. Organometallics 2005; 24: 6077
- 8g Gevorgyan V. Liu J.-X. Rubin M. Benson S. Yamamoto Y. Tetrahedron Lett. 1999; 40: 8919
- 9 Sun C.-L. Shi Z.-J. Chem. Rev. 2014; 114: 9219
- 10a Hreczycho G. Eur. J. Inorg. Chem. 2015; 67
- 10b Hanada S. Motoyama Y. Nagashima H. Eur. J. Org. Chem. 2008; 4097
- 11 Liu ZJ. Lin XL. Yang N. Su ZS. Hu CW. Xiao PH. He YY. Song ZL. J. Am. Chem. Soc. 2016; 138: 1877 ; and references cited therein
- 12a Sakai N. Horikawa S. Ogiwara Y. RSC Adv. 2016; 6: 81763
- 12b Bercot EA. Kindrachuk DE. Rovis T. Org. Lett. 2005; 7: 107
- 12c Mukaiyama T. Izumi J. Shiina I. Chem. Lett. 1997; 187
- 13 Corma A. Iborra S. Velty A. Chem. Rev. 2007; 107: 2411
- 14 Horváth IT. Mehdi H. Fábos V. Boda L. Mika LT. Green Chem. 2008; 10: 238
- 15a Korpaka M. Pietruszkaa J. Adv. Synth. Catal. 2011; 353: 1420
- 15b Adrio LA. Quek LS. Taylor JG. Hii KK. M. Tetrahedron 2009; 65: 10334
- 15c Müller P. Lacrampe F. Bernardinelli G. Tetrahedron: Asymmetry 2003; 14: 1503
- 15d Fang J.-M. Hong B.-C. Liao L.-F. J. Org. Chem. 1987; 52: 855
- 16 Chatterjee B. Mondal D. Bera S. Tetrahedron: Asymmetry 2012; 23: 1170
- 17 Koschker P. Kähny M. Breit B. J. Am. Chem. Soc. 2015; 137: 3131 ; and references cited therein
- 18a Pisani L. Superchi S. D’Elia A. Scafato P. Rosini C. Tetrahedron 2012; 68: 5779
- 18b Ghosh M. Bose S. Ghosh S. Tetrahedron Lett. 2008; 49: 5424
- 18c Zhang Y. Wang Y.-Q. Dai W.-M. J. Org. Chem. 2006; 71: 2445
- 18d Ozeki M. Hashimoto D. Nishide K. Kajimoto T. Node M. Tetrahedron: Asymmetry 2005; 16: 1663
- 19 Nahm S. Weinreb SM. Tetrahedron Lett. 1981; 22: 3815
- 20 Craig II RA. Loskot SA. Mohr JT. Behenna DC. Harned AM. Stoltz BM. Org. Lett. 2015; 17: 5160
For selected reviews, see:
For selected reviews, see:
For selected reviews, see:
For selected seminal works on B(C6F5)3, see:
For related works, see: