An improved synthesis route to functionalized 2-alkyn-1-ylboronates: Useful intermediates for the preparation of α-allenic alcohols

Monatshefte fur Chemie

Volumn 139, Issue 3, 2008, Pages 241-249

  Roy, Chandra D ^a,b   Soundararajan, Raman ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

^b EMD Biosciences Inc   (United States)

Author keywords

Allenic alcohol; (Iodomethyl)boronates; 2 Alkyn 1 ylboronates; Alkynyllithium salts

Indexed keywords

EID: 39749154757     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-007-0769-0     Document Type: Article

References (49)

1. K Tonogaki K Itami J Yoshida 2006 Org Lett 8 1419
2. U Schneider M Sugiura S Kobayashi 2006 Tetrahedron 62 496
3. N Krause ASK Hashmi 2004 Modern Allene Chemistry 1 and 2 Wiley-VCH Weinheim
4. N Krause A Hoffmann-Röder 2004 Tetrahedron 60 11671
5. A Hoffmann-Röder N Krause 2004 Angew Chem Int Ed 43 1196
6. Lee K-C, Lin M-J, Loh T-P (2004) Chem Commun 2456
7. H Yamamoto 1991 BM Trost Comprehensive Organic Synthesis 2 Pergamon Press Oxford 81
8. RW Friesen S Bissada 1994 Tetrahedron Lett 35 5615
9. L-S Li Y-L Wu 2002 Tetrahedron 58 9049
10. T-S Hu Q Yu Y-L Wu Y-K Wu 2001 J Org Chem 66 853
11. JA Marshall Z-H Lu BA Johns 1998 J Org Chem 63 817
12. Marino JP, McClure MS, Holub DP, Comasseto JV, Tucci FC (2002) 124: 1664
13. J Chang LA Paquette 2002 Org Lett 4 253
14. CS Poulsen R Madsen 2002 J Org Chem 67 4441
15. BM Trost JD Chisholm 2002 Org Lett 4 3743
16. H-Y Lee BG Kim 2000 Org Lett 2 1951
17. W Miao LW Chung Y-D Wu TH Chan 2004 J Am Chem Soc 126 13326
18. HC Brown PV Ramachandran 1995 A Hassner Advances in Asymmetric Synthesis 1 JAI Press Greenwich, CT 147
19. E Favre M Gaudemer 1974 J Organomet Chem 297 305
20. R Epsztein 1984 E Buncel T Durst Comprehensive Carbanion Chemistry, Part B Elsevier Amsterdam
21. Favre E, Gaudemar M (1968) Bull Soc Chim Fr: 3724
22. E Favre M Gaudemer 1966 Compt Rend C 263 1543
23. HC Brown UR Khire 1993 Tetrahedron Lett 34 15
24. K Belyk MJ Rozema P Knochel 1992 J Org Chem 57 4070
25. EJ Corey C-M Yu D-H Lee 1990 J Am Chem Soc 112 878
26. DS Matteson 1989 Tetrahedron 45 1859
27. HC Brown SM Singh MV Rangaishenvi 1986 J Org Chem 51 3150
28. KM Sadhu DS Matteson 1985 Organometallics 4 1689
29. Michnik TJ, Matteson DS (1991) Synlett: 631
30. RH Wallace KK Zong 1992 Tetrahedron Lett 33 6941
31. R Soundararajan G Li HC Brown 1994 Tetrahedron Lett 35 8957
32. A Pelter K Smith HC Brown 1988 Borane Reagents Academic Press London
33. R Soundararajan G Li HC Brown 1994 Tetrahedron Lett 35 8961
34. HC Brown NG Bhat M Srebnik 1988 Tetrahedron Lett 29 2631
35. HC Brown CD Roy R Soundararajan 1997 Tetrahedron Lett 38 765
36. MV Rangaishenvi B Singaram HC Brown 1991 J Org Chem 56 3286
37. R Soundararajan G Li HC Brown 1996 J Org Chem 61 100
38. CD Roy HC Brown 2007 J Organomet Chem 692 784
39. CD Roy HC Brown 2007 Monatsh Chem 138 747
40. CD Roy HC Brown 2007 Monatsh Chem 138 879
41. HC Brown GW Kramer AB Levy MM Midland 1975 Organic Syntheses via Borane John Wiley & Sons New York
42. Ogle CA, Wilson TE, Stowe JA (1990) Synthesis: 495
43. JA Marshall X-J Wang 1992 J Org Chem 57 2747
44. HC Brown GA Molander SM Singh US Racherla 1985 J Org Chem 50 1577
45. CC Fortes CFD Garrote 1993 Synth Commun 23 2869
46. OP Vig ML Sharma S Kumari V Rani 1985 Ind J Chem Sect B 24 771
47. RL Danheiser EJ Stoner H Koyama DS Yamashita CA Klade 1989 J Am Chem Soc 111 4407
48. Crombie J (1957) J Chem Soc: 1622
49. IV Ivanov NV Groza GM Mal'chenko GI Myagkova T Shewe 1997 Russ J Bioorg Chem (Engl Transl) 23 481