A New Enantioselective Catalytic
Route to Florhydral®

Sara Bovo; Alberto Scrivanti; Matteo Bertoldini; Valentina Beghetto; Ugo Matteoli

doi:10.1055/s-2008-1067167

PAPER

A New Enantioselective Catalytic Route to Florhydral^®

Sara Bovo, Alberto Scrivanti, Matteo Bertoldini, Valentina Beghetto, Ugo Matteoli*
Dipartimento di Chimica, Università di Venezia, Calle Larga S. Marta 2137, 30123 Venezia, Italy
Fax: +39(041)2348967; e-Mail: matteoli@unive.it;

Abstract

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Abstract

The valuable fragrance Florhydral^® [3-(3-isopropylphenyl)butanal] has been synthesized in almost enantiomerically pure form by a new catalytic route. The key step of the process is the enantioselective hydrogenation of (E)-3-(3-isopropylphenyl)but-2-en-1-ol, which is carried out with asymmetric inductions of up to 97% using an iridium-phosphinooxazoline chiral catalyst.

Key words

enantioselective hydrogenation - asymmetric catalysis - iridium - fragrance asymmetric synthesis - chiral fragrances

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References

<A NAME="RZ08908SS-1">1</A> Abate A. Brenna E. Dei Negri C. Fuganti C. Gatti FG. Serra S. J. Mol. Catal. B: Enzym. 2004, 32: 33

<A NAME="RZ08908SS-2">2</A> Blaser HU. Spindler F. Studer M. Appl. Catal., A. Gen. 2001, 221: 119

<A NAME="RZ08908SS-3">3</A> Bentley R. Chem. Rev. 2006, 106: 4099

<A NAME="RZ08908SS-4">4</A> Sell CS. In Perspectives in Flavor and Fragrance Research Kraft P. Swift KAD. Verlag Helvetica Chimica Acta; Zurich: 2005. p.67

<A NAME="RZ08908SS-5">5</A> Chapuis C. Jacoby D. Appl. Catal., A: Gen. 2001, 221: 93

<A NAME="RZ08908SS-6">6</A> Abate A. Brenna E. Fuganti C. Gatti FG. Serra S. In Perspectives in Flavor and Fragrance Research Kraft P. Swift KAD. Verlag Helvetica Chimica Acta; Zurich: 2005. p.55

<A NAME="RZ08908SS-7">7</A> Brenna E. Fuganti C. Serra S. Tetrahedron: Asymmetry 2003, 14: 1

<A NAME="RZ08908SS-8">8</A> Peck AM. Hornbuckle KC. Atmos. Environ. 2006, 40: 6101

<A NAME="RZ08908SS-9">9</A> Niederer M. Bollhalder R. Hohl C. J. Chromatogr., A 2006, 1132: 109

<A NAME="RZ08908SS-10">10</A> Abate A. Brenna E. Dei Negri C. Fuganti C. Serra S. Tetrahedron: Asymmetry 2002, 13: 899

<A NAME="RZ08908SS-11">11</A> Matteoli U. Ciappa A. Bovo S. Bertoldini M. Scrivanti A. Tetrahedron: Asymmetry 2007, 18: 797

<A NAME="RZ08908SS-12">12</A> Scrivanti A. Bovo S. Ciappa A. Matteoli U. Tetrahedron Lett. 2006, 47: 9261

<A NAME="RZ08908SS-13">13</A> Paganelli S. Ciappa A. Marchetti M. Scrivanti A. Matteoli U. J. Mol. Catal. A: Chem. 2006, 247: 138

<A NAME="RZ08908SS-14A">14a</A> Akutagawa S. Tani K. In Catalytic Asymmetric Synthesis Ojima I. Wiley-VCH; Weinheim: 2000. p.145

<A NAME="RZ08908SS-14B">14b</A> Akutagawa S. In Chirality in Industry Collins AN. Sheldrake GN. Crosby J. Wiley; New York: 1992. Chap. 16. p.325

<A NAME="RZ08908SS-15">15</A> van der Drift RC. Bouwman E. Drent E. J. Organomet. Chem. 2002, 650: 1

<A NAME="RZ08908SS-16">16</A> Tanaka K. Fu GC. J. Org. Chem. 2001, 66: 8177

<A NAME="RZ08908SS-17">17</A> Boeda F. Mosset P. Crévisy C. Tetrahedron Lett. 2006, 47: 5021

<A NAME="RZ08908SS-18">18</A> Ito M. Kitahara S. Ikariya T. J. Am. Chem. Soc. 2005, 127: 6172

<A NAME="RZ08908SS-19">19</A> Tani K. Pure Appl. Chem. 1985, 57: 1845

<A NAME="RZ08908SS-20">20</A> Tani K. Yamagata T. Otsuka S. Kumobayashi H. Akutagawa S. Org. Synth. 1989, 67: 33

<A NAME="RZ08908SS-21">21</A> Ohkuma T. Kitamura M. Noyori R. In Catalytic Asymmetric Synthesis Ojima I. Wiley-VCH; Weinheim: 2000. p.25

<A NAME="RZ08908SS-22">22</A> Tang W. Zhang X. Chem. Rev. 2003, 103: 3029

<A NAME="RZ08908SS-23A">23a</A> Lightfoot A. Schnider P. Pfaltz A. Angew. Chem. Int. Ed. 1998, 37: 2897

<A NAME="RZ08908SS-23B">23b</A> Roseblade SJ. Pfaltz A. Acc. Chem. Res. 2007, 40: 1402

<A NAME="RZ08908SS-23C">23c</A> Wuestenberg B. Pfaltz A. Adv. Synth. Catal. 2008, 350: 174

<A NAME="RZ08908SS-24">24</A> Tang W. Wang W. Zhang X. Angew. Chem. Int. Ed. 2003, 42: 943

<A NAME="RZ08908SS-25">25</A> Li X. Kong L. Gao Y. Wang X. Tetrahedron Lett. 2007, 48: 3915

A New Enantioselective Catalytic Route to Florhydral®

A New Enantioselective Catalytic Route to Florhydral^®