Synthesis of Racemic Tertiary Cyanohydrins

Fu-Xue Chen; Xiaoming Feng

doi:10.1055/s-2005-864831

ACCOUNT

Synthesis of Racemic Tertiary Cyanohydrins

Fu-Xue Chen, Xiaoming Feng*
Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
Fax: +86(28)85418249; e-Mail: xmfeng@scu.edu.cn;

Abstract

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Abstract

The addition of TMS-CN to ketones is catalyzed by homo- and heterogeneous catalysts, which are rationally designed by the line of hydrogen bond activation, dual activation, and the general concept of green chemistry. Especially noteworthy is that those approaches could be readily transferred to enantioselective version of the art. This account describes the development of the catalyst and comparison of the catalytic capacity depending on the nature of the catalyst and structural modifications with mechanism elucidation in appropriate position.

1 Introduction

2 Through Homogeneous Catalysis

2.1 With Lewis Acids

2.2 With Organocatalysts

2.3 With Dual Activation Catalysts

2.3.1 With Bifunctional Catalysts

2.3.2 With Double-Activation Catalysts

3 Through Heterogeneous Catalysis

3.1 Prior Art

3.2 With Inorganic and Organic Salts

4 Summary and Perspectives

Key words

alcohols - catalysis - ketones - nitriles - nucleophilic additions

Full Text

References

<A NAME="RA37104ST-1">1</A> Gregory RJH. Chem. Rev. 1999, 99: 3649

<A NAME="RA37104ST-2A">2a</A> Utimoto K. Wakabayashi Y. Horiie T. Inoue M. Shiahiyama Y. Obayashi M. Nozaki H. Tetrahedron 1983, 39: 967

<A NAME="RA37104ST-2B">2b</A> Grunewald GL. Brouillette WJ. Finney JA. Tetrahedron Lett. 1980, 21: 1219

<A NAME="RA37104ST-2C">2c</A> Evans DA. Carroll GL. Truesdale LK. J. Org. Chem. 1974, 39: 914

<A NAME="RA37104ST-2D">2d</A> Eliel EL. Freeman JP. Org. Synth. Coll. Vol. IV 1963, 58

<A NAME="RA37104ST-2E">2e</A> Kobayashi S. Ishitani H. Chem. Rev. 1999, 99: 1069

<A NAME="RA37104ST-2F">2f</A> Groger H. Chem. Rev. 2003, 103: 2795

<A NAME="RA37104ST-3">3</A> Argranat I. Caner H. Caldwell J. Nat. Rev. Drug Discov. 2002, 1: 753

For a review, see:

<A NAME="RA37104ST-4A">4a</A> Brunel J.-M. Holmes IP. Angew. Chem. Int. Ed. 2004, 43: 2752

<A NAME="RA37104ST-4B">4b</A> North M. Tetrahedron: Asymmetry 2003, 14: 147

<A NAME="RA37104ST-4C">4c</A> North M. Synlett 1993, 807

<A NAME="RA37104ST-5A">5a</A> Evans DA. Truesdale LK. Carroll GL. J. Chem. Soc., Chem. Commun. 1973, 55

<A NAME="RA37104ST-5B">5b</A> Evans DA. Carroll GL. Truesdale LK. J. Org. Chem. 1974, 39: 914

<A NAME="RA37104ST-5C">5c</A> Gassman PG. Talley JJ. Tetrahedron Lett. 1978, 19: 3773

<A NAME="RA37104ST-5D">5d</A> Bian Z.-X. Zhao H.-Y. Li B.-G. Polyhedron 2003, 22: 1523

<A NAME="RA37104ST-5E">5e</A> Moloney MG. Yaqoob M. Synlett 2004, 1631

<A NAME="RA37104ST-6A">6a</A> Bandili M. Cozzi PG. Melchiiorre P. Achille U.-R. Tetrahedron Lett. 2001, 42: 3041

<A NAME="RA37104ST-6B">6b</A> Bandili M. Cozzi PG. Garelli A. Melchiorre P. Achille U.-R. Eur. J. Org. Chem. 2002, 3243

<A NAME="RA37104ST-7">7</A> Lidy W. Sundermeyer W. Chem. Ber. 1973, 106: 587

<A NAME="RA37104ST-8">8</A> Kim SS. Rajagopal G. Song DH. J. Organomet. Chem. 2004, 689: 1734

<A NAME="RA37104ST-9">9</A> Whitesell JK. Apodaca R. Tetrahedron Lett. 1996, 37: 2525

<A NAME="RA37104ST-10">10</A> Jenner G. Tetrahedron Lett. 1999, 40: 491

<A NAME="RA37104ST-11">11</A> Matrubara S. Takai T. Utimoto K. Chem. Lett. 1991, 1447

<A NAME="RA37104ST-12">12</A> Curini M. Epifanio F. Macrotullio MC. Rosati O. Rossi M. Synlett 1999, 315

<A NAME="RA37104ST-13">13</A> Yang Y. Wang D. Synlett 1997, 1379

<A NAME="RA37104ST-14">14</A> Saravanan P. Anand RV. Singh VK. Tetrahedron Lett. 1998, 39: 3823

<A NAME="RA37104ST-15">15</A> Noyori R. Murata S. Suzuki M. Tetrahedron 1981, 38: 3899

<A NAME="RA37104ST-16">16</A> Fujii A. Sakaguchi S. Ishii Y. J. Org. Chem. 2000, 65: 6209

<A NAME="RA37104ST-17">17</A> Wilkinson HS. Grover PT. Vandenbossch CP. Bakale RP. Bhongle NN. Wald SA. Senanayake CH. Org. Lett. 2001, 3: 553

<A NAME="RA37104ST-18">18</A> Greenlee WG. Hangauer DG. Tetrahedron Lett. 1983, 24: 4559

<A NAME="RA37104ST-19">19</A> Marteel AE. Davies JA. Olson WW. Abraham MA. Ann. Rev. Environ. Res. 2003, 28: 401

<A NAME="RA37104ST-20">20</A> Dalko PI. Moisan L. Angew. Chem. Int. Ed. 2004, 43: 5138

<A NAME="RA37104ST-21A">21a</A> Kobayashi S. Tsuchiya Y. Mukaiyama T. Chem. Lett. 1991, 537

<A NAME="RA37104ST-21B">21b</A> Kruchok IS. Gerus II. Kukhar VP. Tetrahedron 2000, 56: 6533

<A NAME="RA37104ST-21C">21c</A> Yadav JS. Reddy BVS. Reddy MS. Prasad AR. Tetrahedron Lett. 2002, 43: 9703

<A NAME="RA37104ST-21D">21d</A> Cordoba R. Csaky AG. Plumet J. Arkivoc 2004, (4): 94

<A NAME="RA37104ST-22A">22a</A> Liu B. Feng X. Chen F.-X. Zhang G. Jiang Y. Synlett 2001, 1551

<A NAME="RA37104ST-22B">22b</A> Jiao Z. Feng X. Liu B. Chen F.-X. Zhang G. Jiang Y. Eur. J. Org. Chem. 2003, 3818

<A NAME="RA37104ST-22C">22c</A> Nakajima M. Saito S. Shiro M. Hashimoto S. J. Am. Chem. Soc. 1997, 120: 6419

<A NAME="RA37104ST-22D">22d</A> Chuit C. Corriu RJP. Reye C. Young JC. Chem. Rev. 1993, 93: 1371

<A NAME="RA37104ST-23">23</A> Kim SS. Kim DW. Rajagopal G. Synthesis 2004, 213

<A NAME="RA37104ST-24">24</A> Li Y. He B. Feng X. Zhang G. Synlett 2004, 1598

<A NAME="RA37104ST-25A">25a</A> Gröger H. Chem.-Eur. J. 2001, 7: 5246

<A NAME="RA37104ST-25B">25b</A> Shibasaki M. Kanai M. Funabashi K. Chem. Commun. 2002, 1989

<A NAME="RA37104ST-25C">25c</A> Ma J.-A. Cahard D. Angew. Chem. Int. Ed. 2004, 43: 4566

<A NAME="RA37104ST-25D">25d</A> Kanemasa S. Ito K. Eur. J. Org. Chem. 2004, 4741

<A NAME="RA37104ST-26A">26a</A> Shen Y. Feng X. Li Y. Zhang G. Jiang Y. Synlett 2002, 793

<A NAME="RA37104ST-26B">26b</A> Shen Y. Feng X. Li Y. Zhang G. Jiang Y. Tetrahedron 2003, 59: 5667

<A NAME="RA37104ST-26C">26c</A> For its enantioselective version, see: Shen Y. Feng X. Zhang G. Jiang Y. Synlett 2002, 1353

<A NAME="RA37104ST-26D">26d</A> Shen Y. Feng X. Li Y. Zhang G. Jiang Y. Eur. J. Org. Chem. 2004, 129

<A NAME="RA37104ST-26E">26e</A> For modification to the catalytically active species, see: He B. Chen F.-X. Li Y. Feng X. Zhang G. Tetrahedron Lett. 2004, 45: 5465

<A NAME="RA37104ST-26F">26f</A> He B. Chen F.-X. Li Y. Feng X. Zhang G. Eur. J. Org. Chem. 2004, 4657

For other examples of asymmetric cyanosilylation of ketones, see:

<A NAME="RA37104ST-27A">27a</A> Hamashima Y. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2000, 122: 7412

<A NAME="RA37104ST-27B">27b</A> Hamashima Y. Kanai M. Shibasaki M. Tetrahedron Lett. 2001, 42: 691

<A NAME="RA37104ST-27C">27c</A> Tian S.-K. Hong R. Deng L. J. Am. Chem. Soc. 2003, 125: 9900

<A NAME="RA37104ST-27D">27d</A> Tian S.-K. Deng L. J. Am. Chem. Soc. 2001, 123: 6195

<A NAME="RA37104ST-27E">27e</A> Deng H. Isler MP. Snapper ML. Hoveyda AH. Angew. Chem. Int. Ed. 2002, 41: 1009

<A NAME="RA37104ST-28A">28a</A> Chen F.-X. Feng X. Arkivoc 2003, (2): 21

<A NAME="RA37104ST-28B">28b</A> Chen F.-X. Feng X. Qin B. Zhang G. Jiang Y. Synlett 2003, 558

<A NAME="RA37104ST-28C">28c</A> Chen F.-X. Liu X. Feng X. Qin B. Zhou H. Zhang G. Synthesis 2004, 2266

<A NAME="RA37104ST-29A">29a</A> Chen F.-X. Feng X. Qin B. Zhang G. Jiang Y. Org. Lett. 2003, 5: 949

<A NAME="RA37104ST-29B">29b</A> Chen F.-X. Qin B. Feng X. Zhang G. Jiang Y. Tetrahedron 2004, 60: 10449

<A NAME="RA37104ST-29C">29c</A> Chen F.-X. Zhou H. Qin B. Feng X. Zhang G. Jiang Y. Chem.-Eur. J. 2004, 10: 4790

<A NAME="RA37104ST-30">30</A> Zhou H. Chen F.-X. Qin B. Feng X. Zhang G. Synlett 2004, 1077

<A NAME="RA37104ST-31">31</A> Anastas PT. Lankey RL. ACS Symposium Series 823 American Chemical Society; Washington D.C.: 2002.

<A NAME="RA37104ST-32A">32a</A> Onaka M. Higuchi K. Sugita K. Izumi Y. Chem. Lett. 1989, 1393

<A NAME="RA37104ST-32B">32b</A> Higuchi K. Onaka M. Izumi Y. J. Chem. Soc., Chem. Commun. 1991, 1035

<A NAME="RA37104ST-32C">32c</A> Izumi Y. Onaka M. J. Mol. Catal. 1992, 74: 35

<A NAME="RA37104ST-33">33</A> Choudary BM. Narender N. Bhuma V. Synth. Commun. 1995, 25: 2829

<A NAME="RA37104ST-34">34</A> Higuchi K. Onaka M. Izumi Y. Bull. Chem. Soc. Jpn. 1993, 66: 2016

<A NAME="RA37104ST-35">35</A> Kantam ML. Sreekanth P. Santi PL. Green Chem. 2000, 47

<A NAME="RA37104ST-36">36</A> Fraile JM. Garcia JI. Mayoral JA. Catal. Today 2000, 57: 3

<A NAME="RA37104ST-37">37</A> He B. Li Y. Feng X. Zhang G. Synlett 2004, 1776