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.

Key words

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 
• 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 

9

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