RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2011(8): 1113-1116
DOI: 10.1055/s-0030-1259933
DOI: 10.1055/s-0030-1259933
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New YorkThe Catalytic Addition of Alkyl Boranes to Alkynyl Esters Affording Single-Isomer Trisubstituted Olefins
Weitere Informationen
Received
16 February 2011
Publikationsdatum:
30. März 2011 (online)
Publikationsverlauf
Publikationsdatum:
30. März 2011 (online)

Abstract
The generation of a series of trisubstituted olefins bearing alkyl substituents is described using a stereoselective and regioselective addition to alkynyl esters. The method produces trisubstituted olefins as single isomers using a convenient and mild transformation in which alkyl boranes are cross-coupled with alkynyl esters and amides using palladium catalysis.
Key words
olefination - stereoselectivity - regioselectivity - cross-coupling - asymmetric synthesis
- 1a
Valentine DH.Hillhouse JH. Synthesis 2003, 317MissingFormLabel - 1b
Rein T.Pedersen TM. Synthesis 2002, 579MissingFormLabel - 1c
Maryanoff BE.Reitz AB. Chem. Rev. 1989, 89: 863MissingFormLabel - 1d
Iorga B.Eymery F.Mouriès V.Savignac P. Tetrahedron 1998, 54: 14637MissingFormLabel - 1e
Wadsworth WS. Org. React. 1977, 25: 73MissingFormLabel - 1f
Nicolaou KC.Bulger PG.Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4490MissingFormLabel - 1g
Grubbs RH. Tetrahedron 2004, 60: 7117MissingFormLabel - 2a
Tan Z.Negishi E. Angew. Chem. Int. Ed. 2006, 45: 762MissingFormLabel - 2b
Tan Z.Negishi E.-I. Angew. Chem. 2006, 118: 776MissingFormLabel - 2c
Marek I. Chem. Rev. 2000, 100: 2887MissingFormLabel - 2d
Hata T.Kitagawa H.Masai H.Kurahashi T.Shimizu M.Hiyama T. Angew. Chem. 2001, 113: 812MissingFormLabel - 2e
Hata T.Kitagawa H.Masai H.Kurahashi T.Shimizu M.Hiyama T. Angew. Chem. Int. Ed. 2001, 40: 790MissingFormLabel - 2f
Kurahashi T.Hata T.Masai H.Kitagawa H.Shimizu M.Hiyama T. Tetrahedron 2002, 58: 6381MissingFormLabel - 2g
Itami K.Mineno M.Muraoka N.Yoshida J. J. Am. Chem. Soc. 2004, 126: 11778MissingFormLabel - 2h
Rossi R.Bellina F.Carpita A.Mazzarella F. Tetrahedron 1996, 52: 4095MissingFormLabel - 2i
Normant JF.Alexakis A. Synthesis 1981, 841MissingFormLabel - 2j
Corey EJ.Katzenellenbogen JA. J. Am. Chem. Soc. 1969, 91: 1851MissingFormLabel - 2k
Negishi E.-i.Zhang Y.Cederbaum FE.Webb MB. J. Org. Chem. 1986, 51: 4080MissingFormLabel - 2l
Itami K.Yoshida J.-i. Bull. Chem. Soc. Jpn. 2006, 79: 811MissingFormLabel - 2m
Itami K.Yoshida J.-i. Chem. Eur. J. 2006, 12: 3966MissingFormLabel - 3a
Chen C.Kehr G.Fröhlich R.Erker G. J. Am. Chem. Soc. 2010, 132: 13594MissingFormLabel - 3b
Zhou C.-Y.Zhu S.-F.Wang L.-X.Zhou Q.-L. J. Am. Chem. Soc. 2010, 132: 10955MissingFormLabel - 3c
Tsuji H.Ueda Y.Ilies L.Nakamura E. J. Am. Chem. Soc. 2010, 132: 11854MissingFormLabel - 3d
Nakao Y.Yada A.Hiyama T. J. Am. Chem. Soc. 2010, 132: 10024MissingFormLabel - 3e
Yang C.-M.Jeganmohan M.Parthasarathy K.Cheng C.-H. Org Lett. 2010, 132: 3610MissingFormLabel - 3f
Hayashi T.Inoue K.Taniguchi N.Ogasawara M. J. Am. Chem. Soc. 2001, 123: 9918MissingFormLabel - 3g
Hall DG.Chapdelaine D.Préville P.Deslongchamps P. Synlett 1994, 660MissingFormLabel - 3h
Houpis IN.Lee J. Tetrahedron 2000, 56: 817MissingFormLabel - 3i
Qian M.Huang Z.Negishi E. Org. Lett. 2004, 6: 1531MissingFormLabel - 3j
Pommier A.Stepanenko V.Jarowicki K.Kocienski PJ. J. Org. Chem. 2003, 68: 4008MissingFormLabel - 3k
Konno T.Daitoh T.Noiri A.Chae J.Ishihara T.Yamanaka H. Org. Lett. 2004, 6: 933MissingFormLabel - 3l
Nishihara Y.Miyasaka M.Okamoto M.Takahashi H.Inoue E.Tanemura K.Takagi K. J. Am. Chem. Soc. 2007, 129: 12634MissingFormLabel - 4a
Corbet J.-P.Mignani G. Chem. Rev. 2006, 106: 2651MissingFormLabel - 4b
Kinney WA.Teleha CA.Thompson AS.Newport M.Hansen R.Ballentine S.Ghosh S.Mahan A.Grasa G.Zanotti-Gerosa A.Dingenen J.Schubert C.Zhou Y.Leo GC.McComsey DF.Santulli RJ.Maryanoff BE. J. Org. Chem. 2008, 73: 2302MissingFormLabel - 4c
Molander GA.Yokoyama Y. J. Org. Chem. 2006, 71: 2493MissingFormLabel - 4d
Liron F.Fosse C.Pernolet A.Roulland E. J. Org. Chem. 2007, 72: 2220MissingFormLabel - 4e
Tan Z.Negishi E.-I. Angew. Chem. Int. Ed. 2006, 45: 762MissingFormLabel - 5
Bush AG.Jiang JL.Payne PR.Ogilvie WW. Tetrahedron 2009, 65: 8502 - 6a
Lin P.-S.Jeganmohan M.Cheng C.-H. Chem. Eur. J. 2008, 14: 11296MissingFormLabel - 6b
Kuº M.Artok A.Ziyanak F.Artok L. Synlett 2008, 2587MissingFormLabel - 6c
Yamamoto Y.Kirai N. Org. Lett. 2008, 10: 5513MissingFormLabel - 6d
Trost BM.Matsubara S.Caringi JJ. J. Am. Chem. Soc. 1989, 111: 8745MissingFormLabel - 6e
Trost BM.McIntosh MC. J. Am. Chem. Soc. 1995, 117: 7255MissingFormLabel - 6f
Trost BM.Frontier AJ. J. Am. Chem. Soc. 2000, 122: 11727MissingFormLabel - 6g
Lindhardt AT.Mantel MLH.Skrydstrup T. Angew. Chem. Int. Ed. 2008, 47: 2668MissingFormLabel - 6h
Yamamoto Y.Kirai N.Harada Y. Chem. Commun. 2008, 2010MissingFormLabel - 7a
Oh CH.Jung HH.Kim KS.Kim N. Angew. Chem. Int. Ed. 2003, 42: 805MissingFormLabel - 7b
Oh CH.Ryu JH. Bull. Korean Chem. Soc. 2003, 24: 1563MissingFormLabel - 7c
Gupta AK.Kim KS.Oh CH. Synlett 2005, 457MissingFormLabel - 8a
Simard-Mercier J.Jiang JL.Ho ML.Flynn AB.Ogilvie WW. J. Org. Chem. 2008, 73: 5899MissingFormLabel - 8b
Rajagopal T.Flynn AB.Ogilvie WW. Tetrahedron 2010, 66: 8739MissingFormLabel