Enantioselective Double Aldol Reactions Involving the Sequential Activation of Silicon Tetrachloride by Chiral Phosphine Oxides

Shunsuke Kotani; Masaharu Sugiura; Makoto Nakajima

doi:10.1055/s-0033-1340600

Synlett, Table of Contents

Synlett 2014; 25(5): 631-640
DOI: 10.1055/s-0033-1340600

account

Enantioselective Double Aldol Reactions Involving the Sequential Activation of Silicon Tetrachloride by Chiral Phosphine Oxides

Shunsuke Kotani

^aPriority Organization for Innovation and Excellence, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto, 862-0973, Japan

,

Masaharu Sugiura

^bGraduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto, 862-0973, Japan Fax: +81(96)3727692 Email: nakajima@gpo.kumamoto-u.ac.jp

,

Makoto Nakajima*

^bGraduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto, 862-0973, Japan Fax: +81(96)3727692 Email: nakajima@gpo.kumamoto-u.ac.jp

› Author Affiliations

Abstract

All articles of this category

Abstract

This account summarizes our recent studies on the development of phosphine oxide-catalyzed enantioselective double aldol reactions that extend hypervalent silicon chemistry by using a Lewis base catalyst. Chiral phosphine oxides repeatedly activate silicon tetrachloride and form hypervalent silicon complexes, thereby promoting sequential activation of substrates and realizing enantioselective double aldol reactions. The account describes several relevant applications of these reactions.

1 Introduction

2 General Concept of Sequential Catalysis by a Lewis Base

2.1 Lewis Base Catalysis with Chlorosilanes

2.2 Phosphine Oxides as Lewis Base Catalysts

3 Branched-Type Double Aldol Reactions

3.1 Enantioselective Branched-Type Double Aldol Reactions Catalyzed by Phosphine Oxides

3.2 Mechanism of the Branched-Type Double Aldol Reactions

3.3 Applications of the Branched-Type Double Aldol Reactions in Enantioselective Syntheses of 2,3-Dihydropyran-4-ones

4 Linear-Type Double Aldol Reactions

4.1 Enantioselective Linear-Type Double Aldol Reactions Catalyzed by Phosphine Oxides

4.2 Mechanism of the Linear-Type Double Aldol Reactions

4.3 Application of the Double Aldol Reactions to the Total Synthesis of (–)-Ericanone

5 Conclusions

Key words

aldol reaction - asymmetric catalysis - multicomponent reaction - silicon - phosphorus - tandem reaction

Full Text

References

References

1a Mukaiyama T, Narasaka K, Banno K. Chem. Lett. 1973; 1011
1b Mukaiyama T, Banno K, Narasaka K. J. Am. Chem. Soc. 1974; 96: 7503

2a Schetter B, Mahrwald R. Angew. Chem. Int. Ed. 2006; 45: 7506
2b Brodmann T, Lorenz M, Schäckel R, Simsek S, Kalesse M. Synlett 2009; 174

For reviews on tandem reactions, see:

3a Tietze LF, Beifuss U. Angew. Chem. Int. Ed. Engl. 1993; 32: 131
3b Tietze LF. Chem. Rev. 1996; 96: 115
3c Parsons PJ, Penkett CS, Shell AJ. Chem. Rev. 1996; 96: 195
3d Nicolaou KC, Montagnon T, Snyder SA. Chem. Commun. 2003; 551
3e Nicolaou KC, Edmons DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134
3f Pellissier H. Tetrahedron 2006; 62: 1619
3g Pellissier H. Tetrahedron 2006; 62: 2143

4a Abiko A, Liu J.-F, Buske DC, Moriyama S, Masamune S. J. Am. Chem. Soc. 1999; 121: 7168
4b Abiko A, Inoue T, Furuno H, Schwalbe H, Fieres C, Masamune S. J. Am. Chem. Soc. 2001; 123: 4605
4c Abiko A, Inoue T, Masamune S. J. Am. Chem. Soc. 2002; 124: 10759
4d Abiko A. Acc. Chem. Res. 2004; 37: 387

5a Boxer MB, Yamamoto H. J. Am. Chem. Soc. 2006; 128: 48
5b Akakura M, Boxer MB, Yamamoto H. ARKIVOC 2007; (x): 337
5c Albert BJ, Yamamoto H. Angew. Chem. Int. Ed. 2010; 49: 2747

6 Habib F, Cook C, Korobkov I, Murugesu M. Inorg. Chim. Acta. 2012; 380: 378

7a Denmark SE, Fujimori S, Pham SM. J. Org. Chem. 2005; 70: 10823
7b Dias LC, de Marchi AA, Ferreira MA. B, Aguilar AM. J. Org. Chem. 2008; 73: 6299
7c Yamaoka Y, Yamamoto H. J. Am. Chem. Soc. 2010; 132: 5354

8 Shimoda Y, Kotani S, Sugiura M, Nakajima M. Chem. Eur. J. 2011; 17: 7992
9 Shimoda Y, Kubo T, Sugiura M, Kotani S, Nakajima M. Angew. Chem. Int. Ed. 2013; 52: 3461

For reviews on Lewis base catalysis, see:

10a Chelucci G, Murineddu G, Pinna GA. Tetrahedron: Asymmetry 2004; 15: 1373
10b Rendler S, Oestreich M. Synthesis 2005; 1727
10c Orito Y, Nakajima M. Synthesis 2006; 1391
10d Malkov AV, Kočovský P. Eur. J. Org. Chem. 2007; 29
10e Denmark SE, Beutner GL. Angew. Chem. Int. Ed. 2008; 47: 1560
10f Benaglia M, Rossi S. Org. Biomol. Chem. 2010; 8: 3824

11a Smyth CP. J. Am. Chem. Soc. 1938; 60: 183
11b Gilkerson WR, Ezell JB. J. Am. Chem. Soc. 1967; 89: 808
11c Hadži D, Klofutar C, Oblak S. J. Chem. Soc. A 1968; 905
11d Arnett EM, Mitchell EJ, Murty TS. S. R. J. Am. Chem. Soc. 1974; 96: 3875

12 Short JD, Attenoux S, Berrisford DJ. Tetrahedron Lett. 1997; 38: 2351
13 Ogawa C, Sugiura M, Kobayashi S. Angew. Chem. Int. Ed. 2004; 43: 6491

14a Nakajima M, Kotani S, Ishizuka T, Hashimoto S. Tetrahedron Lett. 2005; 46: 157
14b Kotani S, Hashimoto S, Nakajima M. Tetrahedron 2007; 63: 3122
14c Kotani S, Shimoda Y, Sugiura M, Nakajima M. Tetrahedron Lett. 2009; 50: 4602
14d Sugiura M, Sato N, Sonoda Y, Kotani S, Nakajima M. Chem. Asian J. 2010; 5: 478
14e Aoki S, Kotani S, Sugiura M, Nakajima M. Chem. Commun. 2012; 48: 5524
14f Kotani S, Sugiura M, Nakajima M. Chem. Rec. 2013; 13: 362

15 For biheteroaromatic diphosphine dioxide catalyzed stereoselective direct aldol reactions, see: Rossi S, Benaglia M, Genoni A, Benincori T, Celentano G. Tetrahedron 2011; 67: 158

16a Brown KJ, Berry MS, Waterman KC, Lingenfelter D, Murdoch JR. J. Am. Chem. Soc. 1984; 106: 4717
16b Shimada T, Kurushima H, Cho Y.-H, Hayashi T. J. Org. Chem. 2001; 66: 8854

17 Nakajima M, Sasaki Y, Shiro M, Hashimoto S. Tetrahedron: Asymmetry 1997; 8: 341
18 Genoni A, Benaglia M, Rossi S, Celentano G. Chirality 2013; 25: 643
19 Zhang P, Han Z, Wang Z, Ding K. Angew. Chem. Int. Ed. 2013; 52: 11054
20 Kotani S, Sugiura M, Nakajima M unpublished results.
21 Ogasawara M, Kotani S, Nakajima H, Furusho H, Miyasaka M, Shimoda Y, Wu W.-Y, Sugiura M, Takahashi T, Nakajima M. Angew. Chem. Int. Ed. 2013; 52: 13798
22 Bennini B, Chulia A, Kaouadji M, Fondanèche P, Allais DP. Tetrahedron Lett. 2011; 52: 1597
23 Dias LC, Kuroishi PK, Polo EC, de Lucca EC. Jr. Tetrahedron Lett. 2013; 54: 980