Synfacts 2007(12): 1320-1320  
DOI: 10.1055/s-2007-991383
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Heterogeneous Catalytic Asymmetric Direct Aldol Reaction in Water

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada
M. Gruttadauria*, F. Giacalone, A. M. Marculescu, P. Lo Meo, S. Riela, R. Noto
Università di Palermo, Italy
Further Information

Publication History

Publication Date:
22 November 2007 (online)

Significance

Polystyrene resin-supported l-proline 1 was used as a catalyst for the direct aldol reaction of aromatic aldehydes 2 and unmodified ketones 3 in water. Thus, the reaction of 2 with 3 (5 equiv) was carried out with 1 (10 mol%) to give the corresponding aldol products 4 and 5 in 25-97% yield (4/5 = 68:32 to >99:1) with 50-98% ee (4) (21 examples). Catalyst 1 was reused four times without any significant loss of catalytic activity. Screening of solvents showed that the reaction proceeded efficiently only in water.