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-00000084.xml
Synthesis 2007(21): 3427-3430
DOI: 10.1055/s-2007-983829
DOI: 10.1055/s-2007-983829
PSP
© Georg Thieme Verlag Stuttgart · New York
Catalytic Enantioselective Reductive Cyclization of Acetylenic Aldehydes via Hydrogenation
Weitere Informationen
Received
20 April 2007
Publikationsdatum:
30. Juli 2007 (online)
Publikationsverlauf
Publikationsdatum:
30. Juli 2007 (online)
Abstract
The reductive cyclization of acetylenic aldehydes is accomplished via rhodium-catalyzed asymmetric hydrogenation. This process provides access to a wide variety of cyclic allylic alcohols in good yields and with high levels of asymmetric induction.
Key words
acetylenic aldehyde - allylic alcohol - hydrogenation - rhodium - reductive cyclization
- For selected reviews encompassing intra- and intermolecular direct reductive coupling of alkynes to carbonyl partners, see:
-
1a
Ojima I.Tzamarioudaki M.Li Z.Donovan RJ. Chem. Rev. 1996, 96: 635 -
1b
Montgomery J. Acc. Chem. Res. 2000, 33: 467 -
1c
Montgomery J.Amarashinghe KKD.Chowdhury SK.Oblinger E.Seo J.Savchenko AV. Pure Appl. Chem. 2002, 74: 129 -
1d
Ikeda S.-I. Angew. Chem. Int. Ed. 2003, 42: 5120 -
1e
Miller KM.Molinaro C.Jamison TF. Tetrahedron: Asymmetry 2003, 14: 3619 -
1f
Montgomery J. Angew. Chem. Int. Ed. 2004, 43: 3890 -
1g
Jang H.-Y.Krische MJ. Acc. Chem. Res. 2004, 37: 653 - Alkyne reductive coupling may be achieved indirectly via alkyne hydrometalation using hydroboranes or Cp2ZrHCl followed by transmetalation to afford organozinc reagents, which participate in catalyzed enantioselective additions to aldehydes:
-
2a
Oppolzer W.Radinov R. Helv. Chim. Acta 1992, 75: 170 -
2b
Oppolzer W.Radinov R. J. Am. Chem. Soc. 1993, 115: 1593 -
2c
Soai K.Takahashi K. J. Chem. Soc., Perkin Trans. 1 1994, 1257 -
2d
Wipf P.Xu W. Tetrahedron Lett. 1994, 35: 5197 -
2e
Wipf P.Xu W. Org. Synth. 1996, 74: 205 -
2f
Wipf P.Ribe S. J. Org. Chem. 1998, 63: 6454 -
2g
Oppolzer W.Radinov RN.El-Sayed E. J. Org. Chem. 2001, 66: 4766 -
2h
Dahmen S.Bräse S. Org. Lett. 2001, 3: 4119 -
2i
Ji J.-X.Qiu L.-Q.Yip CW.Chan ASC. J. Org. Chem. 2003, 68: 1589 -
2j
Lurain AE.Walsh PJ. J. Am. Chem. Soc. 2003, 125: 10677 -
2k
Ko D.-H.Kang S.-W.Kim KH.Chung Y.Ha D.-C. Bull. Korean Chem. Soc. 2004, 25: 35 -
2l
Jeon S.-J.Chen YK.Walsh PJ. Org. Lett. 2005, 7: 1729 -
2m
Jeon S.-J.Fisher EL.Carroll PJ.Walsh PJ. J. Am. Chem. Soc. 2006, 128: 9618 - 3
Ojima I.Tzamarioudaki M.Tsai C.-Y. J. Am. Chem. Soc. 1994, 116: 3643 - 4
Crowe WE.Rachita MJ. J. Am. Chem. Soc. 1995, 117: 6787 - 5
Oblinger E.Montgomery J. J. Am. Chem. Soc. 1997, 119: 9065 -
6a
Tang X.-Q.Montgomery J. J. Am. Chem. Soc. 1999, 121: 6098 -
6b
Tang X.-Q.Montgomery J. J. Am. Chem. Soc. 2000, 122: 6950 -
6c
Mahandru GM.Liu G.Montgomery J. J. Am. Chem. Soc. 2004, 126: 3698 -
6d
Knapp-Reed B.Mahandru GM.Montgomery J. J. Am. Chem. Soc. 2005, 127: 13156 - 7
Huang W.-S.Chan J.Jamison TF. Org. Lett. 2000, 2: 4221 - 8
Miller KM.Huang W.-S.Jamison TF. J. Am. Chem. Soc. 2003, 125: 3442 - 9
Rhee JU.Krische MJ. J. Am. Chem. Soc. 2006, 128: 10674 -
10a
Kong J.-R.Ngai M.-Y.Krische MJ. J. Am. Chem. Soc. 2006, 128: 718 -
10b
Ngai M.-Y.Barchuk A.Krische MJ. J. Am. Chem. Soc. 2007, 129: 280 - 11
Musashi Y.Sakaki S. J. Am. Chem. Soc. 2002, 124: 7588