30.1.1.3 Acyclic O,N-Acetals (Update 2019)

Abstract

This chapter is an update to the earlier Science of Synthesis contribution (Section 30.1.1), which describes synthetic methods and applications of acyclic O,N-acetals in organic synthesis. This update focuses on the enantioselective synthesis of acyclic O,N-acetals via asymmetric catalysis, which has witnessed significant advances in recent years. Also, recent applications of this class of compound in asymmetric organic synthesis are described.

Schlüsselwörter

acyclic O,N-acetals - hemiaminals - hemiaminal ethers - asymmetric catalysis

• 1 Li G, Fronczek FR, Antilla JC. J. Am. Chem. Soc. 2008; 130: 12 216

• 2 Honjo T, Phipps RJ, Rauniyar V, Toste FD. Angew. Chem. 2012; 124: 9822 Angew. Chem. Int. Ed. 2012; 51: 9684

• 3 Kim H, Rhee YH. J. Am. Chem. Soc. 2012; 134: 4011

• 4 Chi Y, Gellman SH. J. Am. Chem. Soc. 2006; 128: 6804

• 5 Ibrahem I, Zhao G.-L, Córdova A. Chem.–Eur. J. 2007; 13: 683

• 6 Terada M, Machioka K, Sorimachi K. Angew. Chem. 2009; 121: 2591 Angew. Chem. Int. Ed. 2009; 48: 2553

• 7 Terada M, Toda Y. J. Am. Chem. Soc. 2009; 131: 6354

• 8 Huang Y.-Y, Chakrabarti A, Morita N, Schneider U, Kobayashi S. Angew. Chem. 2011; 123: 11 317 Angew. Chem. Int. Ed. 2011; 50: 11 121

• 9 Johnson T, Lautens M. Org. Lett. 2013; 15: 4043

• 10 Johnson T, Luo B, Lautens M. J. Org. Chem. 2016; 81: 4923