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Synlett 2006(18): 2973-2976
DOI: 10.1055/s-2006-944211
DOI: 10.1055/s-2006-944211
LETTER
© Georg Thieme Verlag Stuttgart · New York
A Sequential C-N, C-C Bond-Forming Reaction: Direct Synthesis of α-Amino Acids from Terminal Alkynes
Further Information
Received
24 February 2006
Publication Date:
04 August 2006 (online)
Publication History
Publication Date:
04 August 2006 (online)

Abstract
Catalytic hydroamination is combined with the Strecker reaction to yield a one-pot synthesis of α-cyanoamines from terminal alkynes. This methodology is further applied to the synthesis of α-amino acids and α-amino esters.
Key words
amino acids - catalysis - hydroamination - Strecker reaction - synthesis
- For examples of sequential and tandem reaction sequences, see:
-
1a
Sutton AE.Seigal BA.Finnegan DF.Snapper ML. J. Am. Chem. Soc. 2002, 124: 13390 -
1b
Vosburg DA.Vanderwal CD.Sorensen EJ. J. Am. Chem. Soc. 2002, 124: 4552 -
1c
Bressy C.Alberico D.Lautens M. J. Am. Chem. Soc. 2005, 127: 13148 -
1d
Park S.Kim M.Lee D. J. Am. Chem. Soc. 2005, 127: 9410 -
1e
Sarpong R.Su JT.Stoltz BM. J. Am. Chem. Soc. 2003, 125: 13624 -
1f
Denmark SE.Thorarensen A. Chem. Rev. 1996, 96: 137 ; and references cited therein - 2 In addition to numerous articles, a journal Amino Acids has been dedicated to the subject since 1994
- Selected examples of hydroamination:
-
3a
Tillack A.Khedkar V.Jiao H.Beller M. Eur. J. Org. Chem. 2005, 23: 5001 -
3b
Lutete LM.Kadota I.Yamamoto Y. J. Am. Chem. Soc. 2004, 126: 1622 -
3c
Walsh PJ.Baranger AM.Bergman RG. J. Am. Chem. Soc. 1992, 114: 1708 -
3d
Bytschkov I.Doye S. Eur. J. Org. Chem. 2003, 935 -
3e
Hong S.Marks TJ. Acc. Chem. Res. 2004, 39: 673 -
3f
Müller TE.Pleier AK. J. Chem. Soc., Dalton Trans. 1999, 4: 583 -
3g
Johns AM.Utsunomiya M.Incarvito CD.Hartwig JF. J. Am. Chem. Soc. 2006, 128: 1828 -
3h
Kim H.Lee PH.Livinghouse T. Chem. Commun. 2005, 5205 -
3i
Knight PD.Munslow I.O’Shaughnessy PN.Scott P. Chem. Commun. 2004, 894 -
3j
Gribkov DV.Hultzsch KC. Angew. Chem. Int. Ed. 2004, 43: 5542 ; and references cited therein - 4
Li C.Thomson RK.Gillon B.Patrick BO.Schafer LL. Chem. Commun. 2003, 2462 - 5
Zhang Z.Schafer LL. Org. Lett. 2003, 5: 4733 - Other catalyst systems reported to perform anti-Markovnikov hydroamination:
-
6a
Heutling A.Pohlki F.Doye S. Chem. Eur. J. 2004, 10: 3059 -
6b
Tillack A.Castro IG.Hartung CG.Beller M. Angew. Chem. Int. Ed. 2002, 41: 2541 -
6c
Cao C.Shi Y.Odom AL. Org. Lett. 2002, 4: 2853 -
6d
Tillack A.Khedkar V.Beller M. Tetrahedron Lett. 2004, 45: 8875 - 7
Kita M.Kondo M.Koyama T.Yamada K.Matsumoto T.Lee K.-H.Woo J.-T.Uemura D. J. Am. Chem. Soc. 2004, 126: 4794 - 8
Castro IG.Tillack A.Hartung CG.Beller M. Tetrahedron Lett. 2003, 44: 3217 - 9
Enders D.Shilvock JP. Chem. Soc. Rev. 2000, 29: 359 -
10a
Groger H. Chem. Rev. 2003, 103: 2795 -
10b
Yet L. Angew. Chem. Int. Ed. 2001, 40: 875 -
10c
Spino C. Angew. Chem. Int. Ed. 2004, 43: 1764 -
10d
Ooi T.Uematsu Y.Maruoka K. J. Am. Chem. Soc. 2006, 128: 2548 ; and references cited therein - 11
Haak E.Bytschkov I.Doye S. Angew. Chem. Int. Ed. 1999, 38: 3389 - 12
Sigman MS.Vachal P.Jacobsen EN. Angew. Chem. Int. Ed. 2000, 39: 1279 -
13a
Parsons WH.Patchett AA.Bull HG.Schoen WR.Taub D.Davidson J.Combs PL.Springer JP.Gadebusch H.Weissberger B.Valiant ME.Mellin TN.Busch RD. J. Med. Chem. 1988, 31: 1772 -
13b
Yun YK.Godula K.Cao Y.Donaldson WA. J. Org. Chem. 2003, 68: 901 - 14
Verardo G.Geatti P.Pol E.Giumanini AG. Can. J. Chem. 2002, 80: 779