期刊
ORGANIC LETTERS
卷 14, 期 7, 页码 1704-1707出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol300269u
关键词
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资金
- University of Wisconsin-Madison
- NSF [CHE-9208463, CHE-9629688]
- NIH [RR08389-01]
The synthesis of 1,3-diaminated stereotriads via the bis-aziridination of allenes is reported. The reactive 1,4-diazaspiro[2.2]pentane intermediates undergo a mild Bronsted acid-promoted rearrangement to yield 1,3-diaminated ketones in good yields with excellent stereocontrol. Directed reduction of the ketone can be achieved to yield a C-N/C-O/C-N stereotriad in high dr. The ability to transfer the axial chirality of the substrates to the products allows for the facile preparation of enantioenriched stereotriads from allenes in two simple steps.
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