Montmorillonite K10 Catalyzed Nucleophilic Addition Reaction to Aldimines in Water

Abstract

Montmorillonite K10 catalyzed Mannich-type reaction and hydrophosphonylation proceeded smoothly in water at room temperature to give β-amino esters and α-amino phosphonates, respectively, in good to high yields.

water - Montmorillonite K10 - Mannich-type reaction - hydrophosphonylation - imine

References

1 Modern Solvents In Organic Synthesis, In Topics In Current Chemistry, Vol. 206   Knochel P. Houk KN. Kessler H. Springer Verlag; Berlin: 1999. 

2a Li C.-J. Chem. Rev.  1993,  93:  2023 

2b Li C.-J. Chan T.-H. Organic Reactions in Aqueous Media   Wiley; New York: 1997. 

2c Lubineau A. Augé J. Queneau Y. Synthesis  1994,  741 

2d Li C.-J. Tetrahedron  1996,  52:  5643 

2e Organic Reactions in Water   Grieco P. Blackie Academic & Professional; London: 1998. 

2f Lindstrom UM. Chem. Rev.  2002,  102:  2751 

3 Ribe S. Wipf P. Chem. Commun.  2001,  299 

4 Lewis Acids in Organic Synthesis   Vol. I and II:  Yamamoto H. Wiley-VCH; Weinheim: 2000. 

5 Kobayashi S. Eur. J. Org. Chem.  1999,  15 

6a Akiyama T. Takaya J. Kagoshima H. Synlett  1999,  1426 

6b Akiyama T. Takaya J. Kagoshima H. Synlett  1999,  1045 

6c Akiyama T. Takaya J. Kagoshima H. Tetrahedron Lett.  1999,  40:  7831 

6d Akiyama T. Takaya J. Kagoshima H. Adv. Synth. Catal.  2002,  344:  338 

6e Akiyama T. Itoh J. Fuchibe K. Synlett  2002,  1269 

7 Akiyama T. Takaya J. Kagoshima H. Tetrahedron Lett.  2001,  42:  4025 

8a Clark JH. Acc. Chem. Res.  2002,  35:  791 

8b Okuhara T. Chem. Rev.  2002,  102:  3641 

9 Akiyama T. Matsuda K. Fuchibe K. Synlett  2002,  1898 

For reviews on Mannich and Mannich-type reactions, see:

10a Kleinman EF. Comprehensive Organic Synthesis   Vol. 2:  Trost BM. Fleming I. Pergamon; Oxford: 1991.  p.893 

10b Arend M. Westermann B. Risch N. Angew. Chem., Int. Ed.  1998,  37:  1045 

10c Kobayashi S. Ishitani H. Chem. Rev.  1999,  99:  1069 

11 For Montmorillonite K10 catalyzed Mannich-type reaction in organic solvent, see; Onaka M. Ohno R. Yanagiya N. Izumi Y. Synlett  1993,  141 

12 Akiyama T. Sanada M. Fuchibe K. Synlett  2003,  1463 

For examples of the three-component Mannich-type reactions, see:

13a Kobayashi S. Ishitani H. J. Chem. Soc., Chem. Commun.  1995,  1379 

13b Kobayashi S. Busujima T. Nagayama S. Chem. Commun.  1998,  19 

13c Kobayashi S. Busujima T. Nagayama S. Synlett  1999,  545 

13d Manabe K. Mori Y. Kobayashi S. Synlett  1999,  1401 

13e Loh T.-P. Wei L.-L. Tetrahedron Lett.  1998,  39:  323 

13f Loh T.-P. Liung SBKW. Tan K.-L. Wei L.-L. Tetrahedron  2000,  56:  3227 

13g Shimizu M. Itohara S. Synlett  2000,  1828 

13h Shimizu M. Itohara S. Hase E. Chem. Commun.  2001,  2318 

14a Kafarski P. Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem.  1991,  63:  193 

14b Hirschmann R. Smith AB. Taylor C. Benkovic PA. Taylor SD. Yager KM. Sprengeler PA. Benkovic SJ. Science  1994,  265:  234 

14c Smith WW. Bartlett PA. J. Am. Chem. Soc.  1998,  120:  4622 

15 Gröger H. Hammer B. Chem. Eur. J.  2000,  6:  943