Cluster Preface: BINOL Phosphates for Chemistry

Takahiko Akiyama

was born in Kurashiki (Japan) in 1958 and did his undergraduate and graduate studies at The University of Tokyo. After working at Shionogi Research Laboratories, Shionogi & Co., Ltd., as a research chemist, he was appointed as an assistant professor at Ehime University in 1988. He was a visiting scholar at Stanford University from 1992 to 1993. He joined Gakushuin University as an associate professor in 1994 and was promoted to full professor in 1997. He is a recipient of the Chemical Society of Japan Award for Creative Work (2009), Daiichi-Sankyo Award for Medicinal Organic Chemistry (2009), Nagoya Silver Medal (2012), Arthur C. Cope Scholar Award (2016), and Humboldt Research Award (2016). His current research interests include the development of new and useful synthetic methodologies based on the design of novel chiral Brønsted acid catalysts as well as the utilization of transition-metal catalysts.

Abstract

In 2004, BINOL-derived chiral phosphoric acids have been recognized as versatile Brønsted acid catalysts and a range of different catalytic reactions have since been developed. As illustrated in the following cluster, the field is still growing strongly and new catalyst motifs and reactions are currently being developed by groups all over the world. In this preface, a closer look at the synthetic utility of chiral phosphoric acids and their derivatives before 2004 is taken.

Key words

chiral phosphoric acids - asymmetric Brønsted acid catalysis - organocatalysis - enantioselective synthesis

• References

• 1 Akiyama T, Itoh J, Yokota K, Fuchibe K. Angew. Chem. Int. Ed. 2004; 43: 1566
• 2 Yamanaka M, Itoh J, Fuchibe K, Akiyama T. J. Am. Chem. Soc. 2007; 129: 6756
• 3 Uraguchi D, Terada M. J. Am. Chem. Soc. 2004; 126: 5356

Ishihara and co-workers reported in 2010 that the calcium phosphate was the true catalyst for this Mannich reaction, see:
• 4a Hatano M, Moriyama K, Maki T, Ishihara K. Angew. Chem. Int. Ed. 2010; 49: 3823

Also, see:
• 4b Klussmann M, Ratjen L, Hoffmann S, Wakchaure V, Goddard R, List B. Synlett 2010; 2189
• 4c Terada M, Kanomata K. Synlett 2011; 1255

For reviews see:
• 5a Akiyama T, Itoh J, Fuchibe K. Adv. Synth. Catal. 2006; 348: 999
• 5b Akiyama T. Chem. Rev. 2007; 107: 5744-5758
• 5c Terada M. Synthesis 2010; 1929
• 5d Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047
• 6a Prashad M, Hu B, Repi O, Blacklock TJ, Giannousis P. Org. Process Res. Dev. 2000; 4: 55

See also:
• 6b Wilen SH, Qi JZ, Williard PG. J. Org. Chem. 1991; 56: 485
• 7a Jacques J, Fouquey C. Org. Synth. 1989; 67: 1
• 7b Truesdale LK. Org. Synth. 1989; 67: 13
• 8a Alper H, Hamel N. J. Am. Chem. Soc. 1990; 112: 2803

This work has since never been repeated. Also see references 4b,c in:
• 8b Konrad TM, Fuentes JA, Slawin AM. Z, Clarke ML. Angew. Chem. Int. Ed. 2010; 49: 9197
• 9 McCarthy N, McKervey MA, Ye T, McCann M, Murphy E, Doyle MP. Tetrahedron Lett. 1992; 33: 5983
• 10 Pirrung MC, Zhang J. Tetrahedron Lett. 1992; 33: 5987
• 11 Hodgson DM, Stupple PA, Johnstone C. Chem. Commun. 1999; 2185
• 12a Hodgson DM, Stupple PA, Johnstone C. Chem. Commun. 1999; 2185
• 12b Hodgson DM, Petroliagi M. Tetrahedron: Asymmetry 2001; 12: 877
• 12c Hodgson DM, Stupple PA, Pierard FY. T. M, Labande AH, Johnstone C. Chem.–Eur. J. 2001; 7: 4465
• 12d Hodgson DM, Selden DA, Dossetter AG. Tetrahedron: Asymmetry 2003; 14: 3841
• 14 Inanaga J, Sugimoto Y, Hanamoto T. New J. Chem. 1995; 19: 707
• 14 Hanamoto T, Furuno H, Sugimoto Y, Inanaga J. Synlett 1997; 79
• 15a Furuno H, Hanamoto T, Sugimoto Y, Inanaga J. Org. Lett. 2000; 2: 49
• 15b Furuno H, Kambara T, Tanaka Y, Hanamoto T, Kagawa T, Inanaga J. Tetrahedron Lett. 2003; 44: 6129
• 15c Furuno H, Hayano T, Kambara T, Sugimoto Y, Hanamoto T, Tanaka Y, Jin YZ, Kagawa T, Inanagaa J. Tetrahedron 2003; 59: 10509
• 15d Hayano T, Sakaguchi T, Furuno H, Ohba M, Okawa H, Inanaga J. Chem. Lett. 2003; 32: 608

For reviews, see:
• 16a Phipps RJ, Hamilton GL, Toste FD. Nature Chem. 2012; 4: 603
• 16b Mahlau M, List B. Angew. Chem. Int. Ed. 2013; 52: 518
• 16c Brak K, Jacobsen EN. Angew. Chem. Int. Ed. 2013; 52: 534

For reviews, see:
• 17a Zhong C, Shi X. Eur. J. Org. Chem 2010; 2999
• 17b Shao Z, Zhang H. Chem. Soc. Rev. 2009; 38: 2745