Mannich-Type Reaction in Water in the Presence of a Surfactant

Abstract

The effect of sodium dodecyl sulfate (SDS) loading in fluoroboric acid catalyzed Mannich-type reactions of ketene silyl acetals with aldimines was studied. The reaction proceeded smoothly in the presence of 1 mol% of SDS. Formation of small particles was observed by transmission electron microscopy.

Mannich-type reaction - water - imine - surfactant - amino­ ester

References

1a Kleinman EF. In Comprehensive Organic Synthesis   Vol. 2:  Trost BM. Fleming I. Pergamon Press; Oxford: 1991.  p.893 

1b Arend M. Westermann B. Risch N. Angew. Chem. Int. Ed.  1998,  37:  1045 

1c Kobayashi S. Ishitani H. Chem. Rev.  1999,  99:  1069 

For selected examples of Mannich-type reactions, see:

2a Ojima I. Inaba S. Yoshida K. Tetrahedron Lett.  1977,  3643 

2b Pilli RA. Russowsky D. J. Chem. Soc., Chem. Commun.  1987,  1053 

2c Guanti G. Narisano E. Banfi L. Tetrahedron Lett.  1987,  28:  4331 

2d Mukaiyama T. Kashiwagi K. Matsui S. Chem. Lett.  1989,  1397 

2e Mukaiyama T. Akamatsu H. Han JS. Chem. Lett.  1990,  889 

2f Onaka M. Ohno R. Yanagiya N. Izumi Y. Synlett  1993,  141 

2g Ishihara K. Funahashi K. Hanaki N. Miyata M. Yamamoto H. Synlett  1994,  963 

2h Ishihara K. Miyata M. Hattori K. Tada T. Yamamoto H. J. Am. Chem. Soc.  1994,  116:  10520 

2i Miura K. Nakagawa T. Hosomi A. J. Am. Chem. Soc.  2002,  124:  536 

2j Loncaric C. Manabe K. Kobayashi S. Adv. Synth. Catal.  2003,  345:  1187 

For selected examples of metal-catalyzed Mannich-type and Mannich reactions, see:

3a Kobayashi S. Matsubara R. Nakamura Y. Kitagawa H. Sugiura M. J. Am. Chem. Soc.  2003,  125:  2507 

3b Trost BM. Terrell LR. J. Am. Chem. Soc.  2003,  125:  338 

3c Yoshida T. Morimoto H. Kumagai N. Matsunaga S. Shibasaki M. Angew. Chem. Int. Ed.  2005,  44:  3470 

For selected organocatalyzed Mannich and Mannich-type reactions, see:

4a List B. J. Am. Chem. Soc.  2000,  122:  9336 

4b List B. Pojarliev P. Biller WT. Martin HJ. J. Am. Chem. Soc.  2002,  124:  827 

4c Cordova A. Notz W. Zhong G. Betancort JM. Barbas CF. J. Am. Chem. Soc.  2002,  124:  1842 

4d Hayashi Y. Tsuboi W. Ashimine I. Urushima T. Shoji M. Sakai K. Angew. Chem. Int. Ed.  2003,  42:  3677 

4e Mitsumori S. Zhang H. Cheong PH.-Y. Houk KN. Tanaka F. Barbas CF. J. Am. Chem. Soc.  2006,  128:  1040 ; and references cited therein

For chiral Brønsted acid-catalyzed reactions, see:

5a Akiyama T. Itoh J. Yokota K. Fuchibe K. Angew. Chem. Int. Ed.  2004,  43:  1566 

5b Uraguchi D. Terada M. J. Am. Chem. Soc.  2004,  126:  5356 

5c Akiyama T. Saitoh Y. Morita H. Fuchibe K. Adv. Synth. Catal.  2005,  347:  1523 

5d Hasegawa A. Naganawa Y. Fushimi M. Ishihara K. Yamamoto H. Org. Lett.  2006,  8:  3175 

6a Li C.-J. Chem. Rev.  1993,  93:  2023 

6b Li C.-J. Chan T.-H. Organic Reactions in Aqueous Media   John Wiley; New York: 1997. 

6c Lubineau A. Augé J. Queneau Y. Synthesis  1994,  741 

6d Li C.-J. Tetrahedron  1996,  52:  5643 

6e Organic Reactions in Water   Grieco P. Blackie Academic & Professional; London: 1998. 

6f Lindstrom UM. Chem. Rev.  2002,  102:  2751 

7a Akiyama T. Takaya J. Kagoshima H. Synlett  1999,  1426 

7b Akiyama T. Takaya J. Kagoshima H. Synlett  1999,  1045 

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

7d Akiyama T. Takaya J. Kagoshima H. Adv. Synth. Catal.  2002,  344:  338 

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

9

We formerly studied the loading of SDS using a ketene silyl enol ether as a substrate.

10 For a communication of this paper, see: Akiyama T. Itoh J. Fuchibe K. Synlett  2002,  1269 

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

11a Kobayashi S. Ishitani H. Chem. Commun.  1995,  1379 

11b Manabe K. Mori Y. Kobayashi S. Synlett  1999,  1401 

11c Loh T.-P. Wei L.-L. Tetrahedron Lett.  1998,  39:  323 

11d Loh T.-P. Liung SBKW. Tan K.-L. Wei L.-L. Tetrahedron  2000,  56:  3227 

11e Shimizu M. Itohara S. Synlett  2000,  1828 

11f Shimizu M. Itohara S. Hase E. Chem. Commun.  2001,  2318 

12 Narayan S. Muldoon J. Finn MG. Fokin VV. Kolb HC. Sharpless KB. Angew. Chem. Int. Ed.  2005,  44:  3275 

13 Manabe K. Kobayashi S. Org. Lett.  1999,  1:  1965 

14 Alcaide B. Rodriguez-López J. Monge A. Pérez-Garcia V. Tetrahedron  1990,  46:  6799