Diastereoselective Synthesis of trans-β-Lactams Using a Simple Multifunctional Catalyst

Abstract

A catalytic, highly diastereoselective process for the synthesis of trans-β-lactams is reported. This system is based on a phosphonium fluoride precatalyst that both activates the nucleophile and directs the reaction process for high yield and diastereo­selectivity.

Key words

trans-β-lactam - diastereoselectivity - cycloaddition - catalysis - imine - ketene acetal - phosphonium fluoride precatalyst

References and Notes

• For a review on β-lactam antibiotics, see:
• 3a Rolinson GN. J. Antimicrob. Chemother.  1998,  41:  589 
• 3b The Organic Chemistry of β-Lactams   Georg GI. VCH Publications; New York: 1993. ; and references therein
• 4 Adlington RM. Baldwin JE. Chen B. Cooper SL. McCoull W. Pritchard GJ. Howe TJ. Becker GW. Hermann RB. McNulty AM. Neubauer BL. Bioorg. Med. Chem. Lett.  1997,  7:  1689 
• 5 Borthwick AD. Weingarten G. Haley TM. Tomaszewski M. Wang W. Hu Z. Bedard J. Jih H. Yuen L. Mansour TS. Bioorg. Med. Chem. Lett.  1998,  8:  365 
• 6 For a recent review on β-lactam preparation and signifi-cance,see: Fu N. Tidwell TT. Tetrahedron  2008,  64:  10465 
• 7 Staudinger H. Liebigs Ann. Chem.  1907,  356:  51 
• For catalytic methods of trans-β-lactam formation, see:
• 8a Chen R. Yang B. Su W. Synth. Commun.  2006,  36:  3167 
• 8b Takahashi E. Fujisawa H. Yanai T. Mukaiyama T. Chem. Lett.  2005,  34:  994 
• 8c Lee EC. Hodous BL. Bergin E. Shih C. Fu GC. J. Am. Chem. Soc.  2005,  127:  11586 
• 8d Takahashi E. Fujisawa H. Yanai T. Mukaiyama T. Chem. Lett.  2005,  34:  216 
• 8e Weatherwax A. Abraham CJ. Lectka T. Org. Lett.  2005,  7:  3461 
• 8f Townes JA. Evans MA. Queffelec J. Taylor SJ. Morken JP. Org. Lett.  2002,  4:  2537 
• 8g Tanaka H. Hai AKMA. Sadakane M. Okumoto H. Torii S. J. Org. Chem.  1994,  59:  3040 
• 8h Bouthillier G. Mastalerz H. Menard M. Tetrahedron Lett.  1994,  35:  4689 
• 8i Kita Y. Shibata N. Tohjo T. Yoshida N. J. Chem. Soc., Perkin Trans. 1  1992,  1795 
• 8j Colvin EW. McGarry DG. J. Chem. Soc., Chem. Commun.  1985,  539 
• 8k Chiba T. Nagatsuma M. Nakai T. Chem. Lett.  1985,  14:  1343 
• 9 Kobayashi S. Sano T. Mukaiyama T. Chem. Lett.  1989,  18:  1319 
• 10a France S. Wack H. Hafez AM. Taggi AE. Witsil DR. Lectka T. Org. Lett.  2002,  4:  1603 
• 10b France S. Shah M. Weatherwax A. Wack H. Roth J. Lectka T.
  J. Am. Chem. Soc.  2005,  127:  1206 
• 11 Alden-Danforth E. Scerba MT. Lectka T. Org. Lett.  2008,  10:  4951 
• 12a Hafez AM. Dudding T. Wagerle TR. Shah MH. Taggi AE. Lectka T. J. Org. Chem.  2003,  68:  5819 
• 12b Taggi AE. Hafez AM. Wack H. Young B. Ferraris D. Lectka T. J. Am. Chem. Soc.  2002,  124:  6626 
• 12c Taggi AE. Wack H. Hafez AM. France S. Lectka T. Org. Lett.  2002,  4:  627 
• 12d Taggi AE. Hafez AM. Wack H. Young B. Drury WJ. Lectka T. J. Am. Chem. Soc.  2000,  122:  7831 
• 16 Manhas MS. Ghosh M. Bose AK. J. Org. Chem.  1990,  55:  575 
• 17 Otera J. Fujita Y. Fukuzumi S. Synlett  1994,  213 
• 18a Brown SJ. Clark JH. Macquarrie DJ. J. Chem. Soc., Dalton Trans.  1988,  277 
• 18b Tozawa T. Yamane Y. Mukaiyama T. Chem. Lett.  2006,  35:  56 
• 19 Bose AK. Tsai M. Kapur JC. Tetrahedron Lett.  1974,  40:  3547 
• 20 Zhang H. Mitsumori S. Utsumi N. Imai M. Garcia-Delgado N. Mifsud M. Albertshofer K. Cheong PH. Houk KN. Tanaka F. Barbas CF. J. Am. Chem. Soc.  2008,  130:  875 
• 21 Benaglia M. Coozi F. Puglisi A. Eur. J. Org. Chem.  2007,  17:  2865 
• 22 Gennari C. Schimperna G. Venturini I. Tetrahedron  1988,  44:  4221 

1

Current address: Center for Biomedical Research, HIV and AIDS Program, Population Council, 1230 York Avenue, New York, NY 10065, USA.

2

Current address: National Institute of Diabetes and Digestive and Kidney Diseases, 9000 Rockville Pike Building 8 Rm. 1A-19, Bethesda, MD 20892, USA.

13

Use of the corresponding phosphonium phenoxide provided lower yields and a much slower reaction.

14

Control experiments whereby a cis- or mixed-lactam was mixed with the precatalyst or eventual catalyst or phenoxide showed no hint of epimerization.

15

We did see the analogous open, silylated product in the o-QM cyclization reaction, which subsequently cyclized upon fluoride treatment. See ref. 11 for more information.