C-C Bond Formation via N-Phosphoryliminium Ions

Sape S. Kinderman; Jan H. van Maarseveen; Hans E. Schoemaker; Henk Hiemstra; Floris P. J. T. Rutjes

doi:10.1055/s-2004-822376

PAPER

C-C Bond Formation via N-Phosphoryliminium Ions

Sape S. Kinderman^a, Jan H. van Maarseveen^a, Hans E. Schoemaker^a,c, Henk Hiemstra*^a, Floris P. J. T. Rutjes*^a,b
^a J. H. van’t Hoff Institute of Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands
^b Department of Organic Chemistry, NSRIM, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
Fax: +31(24)365 3393; e-Mail: rutjes@sci.kun.nl;
^c DSM Research, Life Science Products, PO Box 18, 6160 MD Geleen, The Netherlands

Abstract

All articles of this category

Abstract

This paper describes preliminary results in the field of rather unexplored nucleophilic additions to N-phosphoryliminium ions. The synthesis of allylic and non-allylic cyclic amidophosphate-based N,O-acetals and their application in C-C bond formation is detailed. In addition, the influence of a chiral auxiliary on the phosphorus atom has been investigated.

Key words

amidophosphate - phosphoryliminium ion - N,O-acetal - ring-closing metathesis - alkoxyallene

Full Text

References

Reviews on N-acyliminium ions:

1a Speckamp WN. Moolenaar MJ. Tetrahedron 2000, 56: 3817

1b Maryanoff BE. Zhang H.-C. Cohen JH. Turchi IJ. Maryanoff CA. Chem. Rev. 2004, 104: 1431

1c Review on N-sulfonyliminium ions: Weinreb SM. Top. Curr. Chem. 1997, 190: 131

2 Shono T. Matsumura Y. Tsubata K. Uchida K. Kanazawa T. Tsuda K. J. Org. Chem. 1984, 49: 3711

3 Okitsu O. Suzuki R. Kobayashi S. J. Org. Chem. 2001, 66: 809 ; and references cited therein

For some entries see:

4a

Via electrochemical oxidation: Ref. 2.

4b Via Diels-Alder reaction: Boger DL. Corbett WL. Curran TT. Kasper AM. J. Am. Chem. Soc. 1991, 113: 1713

4c See also: Boger DL. Kasper AM. J. Am. Chem. Soc. 1989, 11: 1517

4d Via cyclization reactions: Francisco CG. Freire R. Gonzalez CC. Suarez E. Tetrahedron: Asymmetry 1997, 8: 1971

4e See also: Francisco CG. Herrera AJ. Suarez E. Tetrahedron: Asymmetry 2000, 11: 3879

4f See also: Francisco CG. Freire R. Gonzalez CC. Leon EI. Riesco-Fagundo C. Suarez E. J. Org. Chem. 2001, 66: 1861

5 Li S.-O. J. Am. Chem. Soc. 1952, 74: 5959

6 Ramage R. Hopton D. Parrott MJ. J. Chem. Soc., Perkin Trans. 1 1984, 1357

7 Tjen KCMF. Kinderman SS. Schoemaker HE. Hiemstra H. Rutjes FPJT. Chem. Commun. 2000, 699

8 Kinderman SS. de Gelder R. van Maarseveen JH. Schoemaker HE. Hiemstra H. Rutjes FPJT. J. Am. Chem. Soc. 2004, 126: 4100

9 Kinderman SS. Doodeman R. van Beijma JW. Russcher JC. Tjen KCMF. Kooistra TM. Mohaselzadeh H. van Maarseveen JH. Hiemstra H. Schoemaker HE. Rutjes FPJT. Adv. Synth. Catal. 2002, 344: 736

10 See for example: Bull SD. Davies SG. Epstein SW. Leech MA. Ouzman JVA. J. Chem. Soc., Perkin Trans. 1 1998, 2321

11 Alternatively, the amidophosphates can be obtained via H₂O₂ oxidation of phosphoramidites: Hulst R. van Basten A. Fitzpatrick K. Kellogg RM. J. Chem. Soc., Perkin Trans. 1 1995, 2961

12 For related tandem cyclization/addition reactions with amino acetals see: Veerman JJN. Klein J. Aben RWM. Scheeren HW. Kruse CG. van Maarseveen JH. Rutjes FPJT. Hiemstra H. Eur. J. Org. Chem. 2002, 3133

13 Scholl M. Ding S. Lee CW. Grubbs RH. Org. Lett. 1999, 1: 953

14 Brandsma L. Verkruijsse HD. Synthesis of acetylenes allenes and cumulenes, a laboratory manual in Studies in Organic Chemistry Vol. 8: Elsevier; Amsterdam: 1981.

15 Sato T. Nakamura N. Ikeda K. Okada M. Ishibashi H. Ikeda M. J. Chem. Soc., Perkin Trans. 1 1992, 2399