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IsosteviolProline Conjugates as Highly Efficient Amphiphilic Organocatalysts for Asymmetric Three-Component Mannich Reactions in the Presence of Water

✍ Scribed by Ya-Jie An; Chuan-Chuan Wang; Zi-Ping Liu; Jing-Chao Tao

Publisher
John Wiley and Sons
Year
2012
Tongue
German
Weight
235 KB
Volume
95
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

In this work, six isosteviolamino acid conjugates were designed and synthesized through simple condensation on a large scale without protecting group (Scheme). These amphiphilic organocatalysts mediated asymmetric three‐component Mannich reactions of cyclohexanone and anilines with aromatic aldehydes in the presence of H~2~O. Meanwhile, the isosteviolproline conjugate 3b has been established as a highly efficient catalyst (Table 1), and afforded syn‐Mannich products with excellent diastereoselectivities (syn/anti up to 98 : 2) and enantioselectivities (up to >99% ee; Table 3). The transition state of the reaction in the presence of H~2~O is proposed (Fig. 2).

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