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Organocatalyzed direct aldol reaction of silyl glyoxylates for the synthesis of α-hydroxysilanes

Organocatalyzed direct aldol reaction of silyl glyoxylates f...

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中国化学会第十四届全国有机合成化学学术研讨会

作者： Man-Yi Han Xiaoyu Xie Di Zhou Pinhua Li Lei Wang Department of Chemistry Huaibei Normal University Anhui

Due to their structural uniqueness, α-hydroxysilanes have attracted considerable attentions both for their preparation and synthetic utilities, and the development of efficient method for their preparation is highly demanding. In particular, the direct enantioselective installation of silicon into molecules is becoming increasingly significant.1 To date, there are two main strategies for the synthesis of enantiopure α-hydroxysilane:（1） nucleophilic addition with chiral reagent as the substrate.（2） As an alternative synthetic method, the catalytic asymmetric method is considered to be the most appealing. However, the efficient methodology with broad substrate scope in the catalytic asymmetric synthesis of α-hydroxysilanes remains rare. Thus, the development of catalytic asymmetric method for the synthesis of optically active α-hydroxysilanes is highly desirable.2 In connection with our focus on investigating the new synthetic methods, we recently questioned whether it might be possible to direct activate acylsilanes through organocatalysis because acylsilanes can be considered as an aldehyde equivalent. From a synthetic point of view, the direct activation of unactivated acylsilanes is great challenge for organocatalytic asymmetric aldol reaction. To address this issue, a new activation model for acylsilanes is required. In this context, a novel activation model for acylsilanes was developed and realized by organocatalyzed direct aldol reaction of silyl glyoxylates and aldehydes.

关键词： organocatalysis aldol reaction silyl glyoxylates acylsilanes α-hydroxysilanes

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