Tetrahydrofurans from Substituted
Hex-5-yne-1,4-diols

Carolin Schwehm; Max Wohland; Martin E. Maier

doi:10.1055/s-0030-1258109

LETTER

Tetrahydrofurans from Substituted Hex-5-yne-1,4-diols

Carolin Schwehm, Max Wohland, Martin E. Maier*
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
Fax: +49(7071)295135; e-Mail: martin.e.maier@uni-tuebingen.de;

Abstract

All articles of this category

Abstract

It was discovered that substituted hex-5-yne-1,4-diols like 16, 28, and 30 undergo a domino sequence of Meyer-Schuster rearrangement followed by Michael addition forming 2,5-disubstituted tetrahydrofurans in presence of PtCl₂.

Key words

alkynes - domino reaction - Michael addition - organometallic reagents - rearrangement

Full Text

References

<A NAME="RG09810ST-1">1</A> For a recent review, see: Hintermann L. Labonne A. Synthesis 2007, 1121

For some reviews, see:

<A NAME="RG09810ST-2A">2a</A> Hashmi ASK. Chem. Rev. 2007, 107: 3180

<A NAME="RG09810ST-2B">2b</A> Fürstner A. Davies PW. Angew. Chem. Int. Ed. 2007, 46: 3410 ; Angew. Chem. 2007, 119, 3478

<A NAME="RG09810ST-2C">2c</A> Marion N. Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2750 ; Angew. Chem. 2007, 119, 2806

<A NAME="RG09810ST-2D">2d</A> Jimenez-Nunez E. Echavarren AM. Chem. Commun. 2007, 333

<A NAME="RG09810ST-2E">2e</A> Arcadi A. Chem. Rev. 2008, 108: 3266

<A NAME="RG09810ST-2F">2f</A> Gorin DJ. Sherry BD. Toste FD. Chem. Rev. 2008, 108: 3351

<A NAME="RG09810ST-2G">2g</A> Patil NT. Yamamoto Y. Chem. Rev. 2008, 108: 3395

<A NAME="RG09810ST-2H">2h</A> Melchiorre P. Marigo M. Carlone A. Bartoli G. Angew. Chem. Int. Ed. 2008, 47: 6138 ; Angew. Chem. 2008, 120, 6232

<A NAME="RG09810ST-2I">2i</A> Bongers N. Krause N. Angew. Chem. Int. Ed. 2008, 47: 2178 ; Angew. Chem. 2008, 120, 2208

<A NAME="RG09810ST-2J">2j</A> Li Z. Brouwer C. He C. Chem. Rev. 2008, 108: 3239

<A NAME="RG09810ST-2K">2k</A> Fürstner A. Chem. Soc. Rev. 2009, 38: 3208

<A NAME="RG09810ST-3A">3a</A> Kang J.-E. Shin S. Synlett 2006, 717

<A NAME="RG09810ST-3B">3b</A> Belting V. Krause N. Org. Lett. 2006, 8: 4489

<A NAME="RG09810ST-3C">3c</A> Wilckens K. Uhlemann M. Czekelius C. Chem. Eur. J. 2009, 15: 13323

See, for example:

<A NAME="RG09810ST-4A">4a</A> Fürstner A. Hannen P. Chem. Eur. J. 2006, 12: 3006

<A NAME="RG09810ST-4B">4b</A> Jimenez-Nunez E. Molawi K. Echavarren AM. Chem. Commun. 2009, 7327

<A NAME="RG09810ST-4C">4c</A> Kirsch SF. Synthesis 2008, 3183

<A NAME="RG09810ST-5A">5a</A> Liu B. De Brabander JK. Org. Lett. 2006, 8: 4907

<A NAME="RG09810ST-5B">5b</A> Trost BM. Weiss AH. Angew. Chem. Int. Ed. 2007, 46: 7664; Angew. Chem. 2007, 119, 7808

<A NAME="RG09810ST-5C">5c</A> Aponick A. Li C.-Y. Palmes JA. Org. Lett. 2009, 11: 121

<A NAME="RG09810ST-6">6</A> Antoniotti S. Genin E. Michelet V. Genêt J.-P. J. Am. Chem. Soc. 2005, 127: 9976

For some recent reviews, covering the synthesis of spiroacetals, see:

<A NAME="RG09810ST-7A">7a</A> Perron F. Albizati KF. Chem. Rev. 1989, 89: 1617

<A NAME="RG09810ST-7B">7b</A> Yeung K.-S. Paterson I. Chem. Rev. 2005, 105: 4237

<A NAME="RG09810ST-7C">7c</A> Aho JE. Pihko PM. Rissa TK. Chem. Rev. 2005, 105: 4406

<A NAME="RG09810ST-7D">7d</A> Kiyota H. Top. Heterocycl. Chem. 2006, 5: 65

<A NAME="RG09810ST-7E">7e</A> El Sous M. Ganame D. Zanatta S. Rizzacasa MA. ARKIVOC 2006, 105

<A NAME="RG09810ST-8">8</A> Barun O. Kumar K. Sommer S. Langerak A. Mayer TU. Müller O. Waldmann H. Eur. J. Org. Chem. 2005, 4773

<A NAME="RG09810ST-9">9</A> Niggemann J. Bedorf N. Flörke U. Steinmetz H. Gerth K. Reichenbach H. Höfle G. Eur. J. Org. Chem. 2005, 5013

<A NAME="RG09810ST-10A">10a</A> Lorenz M. Kalesse M. Tetrahedron Lett. 2007, 48: 2905

<A NAME="RG09810ST-10B">10b</A> Lorenz M. Kalesse M. Org. Lett. 2008, 10: 4371

<A NAME="RG09810ST-10C">10c</A> Lorenz M. Bluhm N. Kalesse M. Synthesis 2009, 3061

<A NAME="RG09810ST-11A">11a</A> Paterson I. Findlay AD. Anderson EA. Angew. Chem. Int. Ed. 2007, 46: 6699 ; Angew. Chem. 2007, 119, 6819

<A NAME="RG09810ST-11B">11b</A> Paterson I. Findlay AD. Noti C. Chem. Commun. 2008, 6408

<A NAME="RG09810ST-11C">11c</A> Paterson I. Findlay AD. Noti C. Chem. Asian J. 2009, 4: 594

<A NAME="RG09810ST-12">12</A> Kitamura M. Tokunaga M. Ohkuma T. Noyori R. Org. Synth. 1992, 71: 1 ; Org. Synth., Coll. Vol. IX; 1998, 589

<A NAME="RG09810ST-13">13</A> Ono M. Nakamura H. Konno F. Akita H. Tetrahedron: Asymmetry 2000, 11: 2753

<A NAME="RG09810ST-14">14</A> Moore CG. Murphy PJ. Williams HL. McGown AT. Smith NK. Tetrahedron 2007, 63: 11771

<A NAME="RG09810ST-15A">15a</A> Wilk BK. Synth. Commun. 1993, 23: 2481

<A NAME="RG09810ST-15B">15b</A> Aesa MC. Baán G. Novák L. Szántay C. Synth. Commun. 1995, 25: 1545

<A NAME="RG09810ST-16">16</A> Pietruszka J. Witt A. Synthesis 2006, 4266

<A NAME="RG09810ST-17A">17a</A> Frantz DE. Fässler R. Carreira EM. J. Am. Chem. Soc. 2000, 122: 1806

<A NAME="RG09810ST-17B">17b</A> Sasaki H. Boyall D. Carreira EM. Helv. Chim. Acta 2001, 84: 964

<A NAME="RG09810ST-17C">17c</A> Boyall D. Frantz DE. Carreira EM. Org. Lett. 2002, 4: 2605

<A NAME="RG09810ST-18">18</A> In this paper a domino redox-isomerization-oxa-Michael reaction was used to prepare pyrans: Trost BM. Gutierrez AC. Livingston RC. Org. Lett. 2009, 11: 2539

<A NAME="RG09810ST-19A">19a</A> Engel DA. Dudley GB. Org. Lett. 2006, 8: 4027

<A NAME="RG09810ST-19B">19b</A> Egi M. Yamaguchi Y. Fujiwara N. Akai S. Org. Lett. 2008, 10: 1867

<A NAME="RG09810ST-19C">19c</A> Stefanoni M. Luparia M. Porta A. Zanoni G. Vidari G. Chem. Eur. J. 2009, 15: 3940

<A NAME="RG09810ST-19D">19d</A> Ramón RS. Marion N. Nolan SP. Tetrahedron 2009, 65: 1767

<A NAME="RG09810ST-20A">20a</A> Mangion IK. MacMillan DWC. J. Am. Chem. Soc. 2005, 127: 3696

<A NAME="RG09810ST-20B">20b</A> Varseev GN. Maier ME. Org. Lett. 2007, 9: 1461

<A NAME="RG09810ST-20C">20c</A> Kondekar NB. Kumar P. Org. Lett. 2009, 11: 2611

<A NAME="RG09810ST-21">21</A> Suffert J. Toussaint D. J. Org. Chem. 1995, 60: 3550

Supplementary Material

Supporting Information (PDF)