TBuOLi-mediated alkynylation of aldehydes

Synthetic Communications

Volumn 41, Issue 8, 2011, Pages 1208-1217

  Li, Chuanbin ^a   Li, Xiaolong ^a   Meng, Xu ^a   Wang, Tiansheng ^a   Li, Jihui ^a   Chen, Baohua ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Alkynylation; lithium tert butoxide; propargylic alcohol

Indexed keywords

1 (2 BROMOPHENYL) 2 (CHLOROPHENYL)PROP 2 YN 1 OL; 1 (2 BROMOPHENYL) 3 (NAPHTHALENE 1 YL)PROP 2 YN 1 OL; 1 (2 BROMOPHENYL) 3 PHENYLPROP 2 YN 1 OL; 1 (2 CHLOROPHENYL) 3 (THIOPHEN 3 YL)LPROP 2 YN 1 OL; 1 (2 CHLOROPHENYL) 3 PHENYLPROP 2 YN 1 OL; 1 (2 METHOXYPHENYL) 3 PHENYLPROP 2 YN 1 OL; 1 (2,4 DICHLOROPHENYL) 3 PHENYLPROP 2 YN 1 OL; 1 (3,4 DIMETHYLPHENYL) 3 PHENYLPROP 2 YN 1 OL; 1 (4 CHLOROPHENYL) 3 3 TOLYLPROP 2 YN 1 OL; 1 (4 CHLOROPHENYL) 3 PHENYLPROP 2 YN 1 OL; 1 (4 FERROCENYLPHENYL) 3 PHENYLPROP 2 YN 1 OL; 1 (4 METHOXYPHENYL) 3 PHENYLPROP 2 YN 1 OL; 1 (BENZO(D)(1,3)DIOXO 5 YL) 3 PHENYLPROP 2 YN 1 OL; 1 FERROCENYL 3 PHENYLPROP 2 YN 1 OL; 1 PHENYL 3 (PYRIDIN 3 YL)PROP 2 YN 1 OL; 1,3 DIPHENYLPROP 2 YN 1 OL; 3 (4 FLUOROPHENYL) 1 (FURAN 2 YL)PROP 2 YN 1 OL; 3 (4 FLUOROPHENYL) 1 PHENYLPROP 2 YN 1 OL; 3 (4 METHOXYPHENYL) 1 PHENYLPROP 2 YN 1 OL; 3 PHENYL 1 4 TOLYLPROP 2 YN 1 OL; ALCOHOL DERIVATIVE; ALDEHYDE; LITHIUM TERT BUTOXIDE; N,N DIMETHYLFORMAMIDE; PROPARGYLIC ALCOHOL; REAGENT; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; THIN LAYER CHROMATOGRAPHY;

EID: 79952968432     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.481740     Document Type: Article

References (41)

1. For recent reviews, see (a) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Acetylenes in catalysis: Enantioselective additions to carbonyl groups and imines and applications beyond. Eur. J. Org. Chem. 2004, 4095;
2. Pu, L. Asymmetric alkynylzinc additions to aldehydes and ketones. Tetrahedron 2003, 59, 9873; (b)
3. Rajaram, A. R.; Pu, L. Regiospecific hydration of c-hydroxy-a,b- acetylenic esters: A novel asymmetric synthesis of tetronic acids. Org. Lett. 2006, 8, 2019; (c)
4. Lin, L.; Jiang, X. X.; Liu, W. X.; Qiu, L.; Xu, Z. Q.; Xu, J. K.; Chan, A. S. C.; Wang, R. Highly enantioselective synthesis of c-hydroxy-a,bacetylenic esters catalyzed by a b-sulfonamide alcohol. Org. Lett. 2007, 9, 2329; (d)
5. Li, Z.-B.; Liu, T. D.; Pu, L. Chiral macrocycle-catalyzed highly enantioselective phenylacetylene addition to aliphatic and vinyl aldehydes. J. Org. Chem. 2007, 72, 4340; (e)
6. Koyuncu, H.; Dogan, Ö . Fam-Ti-catalyzed enantioselective alkynylation of aldehydes. Org. Lett. 2007, 9, 3477. (f)
7. Hari, Y.; Date, K.; Aoyama, T. Facile one-pot synthesis of functionalized acetylenes from aryl and heteroaryl aldehydes using lithium trimethylsilyldiazomethane. Heterocycles 2007, 74, 545; (a)
8. Hoffmann-Roder, A.; Krause, N. Synthesis of highly functionalized propargylic alcohols: Direct addition of epoxy acetylides to aldehydes and ketones. Helv. Chim. Acta 2002, 85, 3176; (b)
9. Mortier, J.; Vaultier, M.; Carreaux, F.; Douin, J.-M. Disproportionation of monolithium acetylide into dilithium carbide and acetylene is a reversible reaction in tetrahydrofuran at 0-C. J. Org. Chem. 1998, 63, 3515; (c)
10. Ahn, J. H.; Sim, T. B.; Joung, M. J.; Yoon, N. M. Lithium trimethylalkynylaluminate, a new chemoselective alkynylating agent. Bull. Kor. Chem. Soc. 1996, 17, 380. (d)
11. Stang, P. J.; Diederich, F. Modern Acetylene Chemistry; VCH: Weinheim, 1995.
12. Imamoto, T.; Sugiura, Y.; Takiyama, N. Organocerium reagents: Nucleophilic addition to easily enolizable ketones. Tetrahedron Lett. 1984, 25, 4233.
13. Brown, H. C.; Molander, G. A.; Singh, S. M.; Racherla, U. S. Organoboranes, 38: A facile and highly efficient addition of B-1-alkynyl-9-borabicyclo [3.3.1] nonanes to aldehydes and ketones: An exceptionally chemoselective synthesis of propargylic alcohols. J. Org. Chem. 1985, 50, 1577.
14. Hirao, T.; Misu, D.; Agawa, T. Versatile synthesis of a,b-acetylenic ketones by oxidative nucleophilic addition of vanadium acetylides. Tetrahedron Lett. 1986, 27, 933.
15. Ahn, J. H.; Joung, M. J.; Yoon, N. M.; Oniciu, D. C.; Katritzky, A. R. A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates. J. Org. Chem. 1999, 64, 488; (a)
16. Ahn, J. H.; Joung, M. J.; Yoon, N. M. Sodium diethyldialkylaluminate: A new chemoselective alkynylating agent. J. Org. Chem. 1995, 60, 6173. (b)
17. Yamaguchi, M.; Hayashi, A.; Minami, T. Tin ditriflate-promoted addition of 1-alkynes to aldehydes. J. Org. Chem. 1991, 56, 4091; (a)
18. Yamaguchi, M.; Hayashi, A.; Hirama, M. Direct formation of reactive alkynyltrichlorotins from 1-alkynes, SnCl4, and Bu3N: A mild alkynylation reagent of aldehydes, acetals, and enones. Chem. Lett. 1992, 21, 2479. (b)
19. Han, Y.; Huang, Y. Z. A straightforward, efficient, and versatile preparation of propargylic alcohols from 1-alkynes and aldehydes via GaI3 and amine. Tetrahedron Lett. 1995, 36, 7277.
20. Frantz, D. E.; Fassler, R.; Carreira, E. M. Catalytic in situ generation of Zn(II)-alkynilides under mild conditions: A novel C=N addition process utilizing terminal acetylenes. J. Am. Chem. Soc. 1999, 121, 11245; (a)
21. Jiang, B.; Si, Y. G. Alkynylation of carbonyl compounds with terminal acetylenes promoted by ZnCl2 and Et3N: Simple, mild, and efficient preparation of propargylic alcohols. Tetrahedron Lett. 2002, 43, 8323. (b)
22. Harada, S.; Takita, R.; Ohshima, T.; Matsunaga, S.; Shibasaki, M. Ligand-accelerated indium(III)-catalyzed asymmetric alkynylation of aldehydes with 2-methyl-3-butyn-2-ol as an ethyne equivalent donor. Chem. Commun. 2007, 948; (a)
23. Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. A new entry in catalytic alkynylation of aldehydes and ketones: Dual activation of soft nucleophiles and hard electrophiles by an indium(III) catalyst. Org. Lett. 2005, 7, 1363; (b)
24. Tsuji, R.; Yakura, K.; Ohshima, T.; Shibasaki, M. Asymmetric alkynylation of aldehydes catalyzed by an In(III)=BINOL complex. J. Am. Chem. Soc. 2005, 127, 13760; (c)
25. Sakai, N.; Hirasawa, M.; Konakahara, T. InBr3- Et3N-promoted alkynylation of aldehydes and N,O-acetals under mild conditions: Facile and simple preparation of propargylic alcohols and amines. Tetrahedron Lett. 2003, 44, 4171. (d)
26. For recent representative examples, see (a) Wang, Q.; Chen, S. Y.; Yu, X.-Q.; Pu, L. 1,10-Binaphthyl ligands with bulky 3,30-tertiaryalkyl substituents for the asymmetric alkyne addition to aromatic aldehydes. Tetrahedron 2007, 63, 4422;
27. Wolf, C.; Liu, S. L. Bisoxazolidine-catalyzed enantioselective alkynylation of aldehydes. J. Am. Chem. Soc. 2006, 128, 10996; (b)
28. Trost, B. M.; Weiss, A. H.; Wangelin, A. J. Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes. J. Am. Chem. Soc. 2006, 128, 8; (c)
29. Blay, G.; Fernandez, I.; Marco-Aleixandre, A.; Pedro, J. Mandelamide- zinc-catalyzed enantioselective alkyne addition to heteroaromatic aldehydes. J. Org. Chem. 2006, 71, 6674; (d)
30. Fang, T.; Du, D. M.; Lu, S. F.; Xu, J. X. Synthesis of C3-symmetric tris(b-hydroxy amide) ligands and their Ti(IV) complex-catalyzed enantioselective alkynylation of aldehydes. Org. Lett. 2005, 7, 2081; (e)
31. Ni, M.; Wang, R.; Han, Z. J.; Mao, B.; Da, C. S.; Liu, L.; Chen, C. Synthesis of new C2-symmetrical bissulfonamide ligands and application in the enantioselective addition of alkynylzinc to aldehydes and ketones. Adv. Synth. Catal. 2005, 347, 1659; (f)
32. Weil, T.; Schreiner, P. R. Organocatalytic alkynylation of aldehydes and ketones under phase-transfer catalytic conditions. Eur. J. Org. Chem. 2005, 2213; (g)
33. Cozzi, P. G.; Rudolph, J.; Bolm, C.; Norrby, P. O.; Tomasini, C. Me2Zn-mediated addition of acetylenes to aldehydes and ketones. J. Org. Chem. 2005, 70, 5733; (h)
34. Liu, L.; Pu, L. 3,30-Functionalized octahydro-BINOL: A facile synthesis and its high enantioselectivity in the alkyne addition to aldehydes. Tetrahedron 2004, 60, 7427; (i)
35. Dahmen, S. New ring-expansion reactions of hydroxy propenoyl cyclic compounds under palladium(0)=phosphine-catalyzed conditions. Org. Lett. 2004, 6, 2113. (j)
36. Downey, C. W.; Mahoney, B. D.; Lipari, V. R. Trimethylsilyl trifluoromethanesulfonate- accelerated addition of catalytically generated zinc acetylides to aldehydes. J. Org. Chem. 2009, 74, 2904.
37. Xu, Z.; Wu, N.; Ding, Z.; Wang, T.; Mao, J.; Zhang, Y. l-Proline-derived tertiary amino alcohol as a new chiral ligand for enantioselective alkynylation of aldehydes. Tetrahedron Lett. 2009, 50, 926.
38. Ruan, J.; Lu, G.; Xu, L.; Li, Y.-M.; Chan, A. S. C. Catalytic asymmetric alkynylation and arylation of aldehydes by an H8-binaphthyl-based amino alcohol ligand. Adv. Synth. Catal. 2008, 350, 76.
39. Liu, Q.-Z.; Xie, N.-S.; Luo, Z.-B.; Cui, X.; Cun, L.-F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. Facile preparation of optically pure 7,70-disubstituted BINOLs and their application in asymmetric catalysis. J. Org. Chem. 2003, 68, 7921.
40. Yoshizawa, K.; Shioiri, T. Siloxyallenes revisited: A useful functional intermediate for the synthesis of (Z)-b-branched Morita-Baylis-Hillman type adducts and (Z)-chalcones. Tetrahedron 2007, 63, 6259.
41. Kitazawa, T.; Minowa, T.; Teruaki, M. Lewis base-catalyzed alkynylation of carbonyl compounds with trimethylsilylacetylenes. Chem. Lett. 2006, 35, 1002.