CBS Oxazaborolidines - Versatile Catalysts for Asymmetric Synthesis

SPOTLIGHT

René T. Stemmler*
Institut für Organische Chemie der RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
e-Mail: rene.stemmler@oc.rwth-aachen.de;

For reviews, see:

1a Cho BT. Tetrahedron 2006, 62: 7621

1b Cho BT. Aldrichimica Acta 2002, 35: 3

1c Corey EJ. Helal CJ. Angew. Chem. Int. Ed. 1998, 37: 1986; Angew. Chem. 1998, 110: 2092

1d Itsuno S. Org. React. 1998, 52: 395

CBS represents the initials of the researchers who discovered the reagents 1a-c, namely Corey, Bakshi, and Shibata:

2a Corey EJ. Bakshi RK. Shibata S. J. Am. Chem. Soc. 1987, 109: 5551

2b Corey EJ. Bakshi RK. Shibata S. Chen C.-P. Singh VK. J. Am. Chem. Soc. 1987, 109: 7925

3a Demir AS. Sesenoglu Ö. Ülkü D. Arici C. Helv. Chim. Acta 2003, 86: 91

3b Demir AS. Sesenoglu Ö. Aksoy-Cam H. Kaya H. Aydogan K. Tetrahedron: Asymmetry 2003, 14: 1335

3c Demir AS. Sesenoglu Ö. Gerçek-Arkin Z. Tetrahedron: Asymmetry 2001, 12: 2309

4a Gosselin F. O’Shea PD. Roy S. Reamer RA. Chen C.-y. Volante RP. Org. Lett. 2005, 7: 355

4b Kirton EHM. Tughan G. Morris RE. Field RA. Tetrahedron Lett. 2004, 45: 853

5 Uenishi J. Ohmi M. Angew. Chem. Int. Ed. 2005, 44: 2756 ; Angew. Chem. 2005, 117: 2816

6 Matsuo G. Kawamura K. Hori N. Matsukura H. Nakata T. J. Am. Chem. Soc. 2004, 126: 14374

7 Kita Y. Matsuda S. Fujii E. Horai M. Hata K. Fujioka H. Angew. Chem. Int. Ed. 2005, 44: 5857 ; Angew. Chem. 2005, 117: 6007

8 Crimmins MT. DeBaillie AC. J. Am. Chem. Soc. 2006, 128: 4936

9a Molander GA. George KM. Monovich LG. J. Org. Chem. 2003, 68: 9533

9b Bringmann G. Pabst T. Henschel P. Kraus J. Peters K. Peters E.-M. Rycroft DS. Connolly JD. J. Am. Chem. Soc. 2000, 122: 9127

10a Abe H. Takeda S. Fujita T. Nishioka K. Takeuchi Y. Harayama T. Tetrahedron Lett. 2004, 45: 2327

10b Bringmann G. Menche D. Kraus J. Mühlbacher J. Peters K. Peters E.-M. Brun R. Bezabih M. Abegaz BM. J. Org. Chem. 2002, 67: 5595

10c Bringmann G. Ochse M. Götz R. J. Org. Chem. 2000, 65: 2069

11 For a review, see: Bolm C. Rantanen T. Schiffers I. Zani L. Angew. Chem. Int. Ed. 2005, 44: 1758 ; Angew. Chem. 2005, 117: 1788

12a Hong S. Corey EJ. J. Am. Chem. Soc. 2006, 128: 1346

12b Ryu DH. Corey EJ. J. Am. Chem. Soc. 2003, 125: 6388

12c Zhou G. Hu Q.-Y. Corey EJ. Org. Lett. 2003, 5: 3979

12d Corey EJ. Shibata T. Lee TW. J. Am. Chem. Soc. 2002, 124: 3808

12e Ryu DH. Lee TW. Corey EJ. J. Am. Chem. Soc. 2002, 124: 9992

13 Ryu DH. Corey EJ. J. Am. Chem. Soc. 2004, 126: 8106

14 Liu D. Hong S. Corey EJ. J. Am. Chem. Soc. 2006, 128: 8160

15 Boeckman RK. Pero JE. Boehmler DJ. J. Am. Chem. Soc. 2006, 128: 11032

16 Compounds (S)-1b, (R)-1b, and (S)-o-tolyl-CBS-oxaza-borolidine are commercially available