Download PDF
Synfacts 2010(9): 1065-1065  
DOI: 10.1055/s-0030-1257968
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Hydroxymethylation of Oxindoles

Contributor(s): Benjamin List, Saihu Liao
X.-L. Liu, Y.-H. Liao, Z.-J. Wu, L.-F. Cun, X.-M. Zhang, W.-C. Yuan*
Chengdu Institute of Organic Chemistry, Chengdu Institute of Biological Products and Graduate School of Chinese Academy of Sciences, Beijing, P. R. China
Further Information

Publication History

Publication Date:
23 August 2010 (online)

    Permissions and Reprints

Significance

A thiourea amine bifunctional catalyst promoting hydroxymethylation of oxindoles is presented by the authors. In this transformation, paraformaldehyde was employed as C1 source. With 5 mol% of catalyst 4, the addition of oxindoles 1 to formaldehyde proceeded smoothly at room temperature in 1,2-dichloroethane, furnishing the hydroxymethylation products 3 in high yields and high enantioselectivities. This reaction is proposed to proceed via a double activation mechanism as shown in the Scheme. The N-Boc protecting group is crucial to achieve high enantio-selectivity. Other protecting groups, such as Me or Bn, resulted in very low enantioselectivities.