Asymmetric Synthesis of Diarylmethanols: Development of a Hemilabile Phosphorus Ligand Based on the Concept of Conformational Control

Takafumi Arao; Kiyoto Suzuki; Kazuhiro Kondo; Toyohiko Aoyama

doi:10.1055/s-2006-950315

PAPER

Asymmetric Synthesis of Diarylmethanols: Development of a Hemilabile Phosphorus Ligand Based on the Concept of Conformational Control

Takafumi Arao, Kiyoto Suzuki, Kazuhiro Kondo*, Toyohiko Aoyama*
Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan
Fax: +81(52)8363439; e-Mail: kazuk@phar.nagoya-cu.ac.jp; e-Mail: aoyama@phar.nagoya-cu.ac.jp;

Abstract

All articles of this category

Abstract

The asymmetric synthesis of diarylmethanols using a new hemilabile phosphorus ligand based on the concept of conformational control is described.

Keywords

chiral ligand - asymmetric synthesis - diarylmethanol - rhodium catalyst - boronic acid

Full Text

References

1a Kondo K. Kazuta K. Fujita H. Sakamoto Y. Murakami Y. Tetrahedron 2002, 58: 5209

1b Horibe H. Kazuta K. Kotoku M. Kondo K. Okuno H. Murakami Y. Aoyama T. Synlett 2003, 2047

1c Horibe H. Fukuda Y. Kondo K. Okuno H. Murakami Y. Aoyama T. Tetrahedron 2004, 60: 10701

1d Arao T. Kondo K. Aoyama T. Tetrahedron Lett. 2006, 47: 1417

2 For a review of hemilabile ligands, see: Grushin VV. Chem. Rev. 2004, 104: 1629

3a Oxazaborolidine-catalyzed reduction: Corey EJ. Helal CJ. Tetrahedron Lett. 1995, 36: 9153

3b Ru-BINAP catalyzed hydrogenation: Ohkuma T. Koizumi M. Ikehira H. Yokozawa T. Noyori R. Org. Lett. 2000, 2: 659 ; and references cited therein

Rhodium-catalyzed asymmetric arylation of aromatic aldehyde:

4a Sakai M. Ueda M. Miyaura N. Angew. Chem. Int. Ed. 1998, 37: 3279

4b Moreau C. Hague C. Weller AS. Frost CG. Tetrahedron Lett. 2001, 42: 6957

4c Focken T. Rudolph J. Bolm C. Synthesis 2005, 429

4d Suzuki K. Kondo K. Aoyama T. Synthesis 2006, 1360

For a quite recent review:

4e Schmidt F. Stemmler RT. Rudolph J. Bolm C. Chem. Soc. Rev. 2006, 35: 454

For a practical successful example, see the copper-catalyzed arylation:

4f Tomita D. Wada R. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2005, 127: 4138

4g Tomita D. Kanai M. Shibasaki M. Chem. Asian J. 2006, 1: 161

For a rhodium-catalyzed asymmetric arylation of isatin, see:

4h Shintani R. Inoue M. Hayashi T. Angew. Chem. Int. Ed. 2006, 45: 3353

5 Uozumi Y. Hayashi T. J. Am. Chem. Soc. 1991, 113: 9887

6 For our preliminary communication, see: Suzuki K. Ishii S. Kondo K. Aoyama T. Synlett 2006, 648

7 Morimoto T. Chiba M. Achiwa K. Tetrahedron Lett. 1989, 30: 735

8a van der Stelt C. Heus WJ. Nauta WT. Arzneim.-Forsch. 1969, 19: 2010

8b Casy AF. Drake AF. Ganellin CR. Mercer AD. Upton C. Chirality 1992, 4: 356

8c Ohkuma T. Koizumi M. Ikehara H. Yokozawa T. Noyori R. Org. Lett. 2000, 2: 659

Application of organic reactions with phosphonium salts:

9a Netherton MR. Fu GC. Org. Lett. 2001, 3: 4295

9b Danjo H. Sasaki W. Miyazaki T. Imamoto T. Tetrahedron Lett. 2003, 44: 3467

Application of organic reactions with metal-catecholborane complex:

9c Miyazaki T. Sugawara M. Danjo H. Imamoto T. Tetrahedron Lett. 2004, 45: 9341

For a bifunctional asymmetric catalysis, see:

10a Shibasaki M. Kanai M. Funabashi K. Chem. Commun. 2002, 1989

10b Kanai M. Kato N. Ichikawa E. Shibasaki M. Synlett 2005, 1491

11

Fukuda, Y.; Kondo, K.; Aoyama, T. submitted for publication.

12 Carmack M. Kelley CJ. J. Org. Chem. 1968, 33: 2171

13 Huang W.-S. Pu L. J. Org. Chem. 1999, 64: 4222

14 Seebach D. Beck AK. Roggo S. Wonnacott A. Chem. Ber. 1985, 118: 3673

15 Wang Z. Chandler WD. Lee DG. Can. J. Chem. 1998, 76: 919

16 Naito J. Chirality 2003, 16: 22