Asymmetric Domino Reaction of N-Sulfonylimines and α,β-Unsaturated Aldehydes Undergoing a Different

• 作 者: Qianjin An Wanbin Zhang
• 机 构: SchoolofPharmacy,ShanghaiJiaoTongUniversityShanghai200240SchoolofPharmacy,ShanghaiJiaoTongUniversity
• 出 处: 中国化学会全国第十一届有机合成化学学术研讨会
• 发表日期: 2014年10期
• 关键词: Organocatalyzed domino reaction cyclic N-sulfonylimine chiral nitrogen-containin

Organocatalyzed asymmetric domino reactions have experienced a rapid progress because such reactions can provide two or more bond-forming transformations concurrently in one reaction procedure.1 We have adopted this tactic utilizing easily accessible substrates to construct an all-carbon cyclopentane ring system with four contiguous stereocenters.2 And then organocatalyzed asymmetric domino reactions of amino aldehyde and aldehyde esters toβ,γ-unsaturated α-keto esters were also designed, affording oxygen-containing pyran rings with excellent asymmetric behavior.3This time, we have developed an efficient organocatalyzed asymmetric domino reaction of cyclic N-sulfonylimines with a, β-unsaturated aldehydes for the synthesis of medicinally interesting and synthetically challenging piperidine ring intermediates containing two stereocenters.It was found that the reaction proceeds via a different pathway to that involving simple aldehydes,4 affording the desired products in good yields (up to 93％), and with excellentenantioselectivities (up to ＞99％), and diastereoselectivities (up to ＞20∶1).