In Situ Generation Technology of β-Butoxycarbonyliodonium Ylide: A Hypervalent Analogue of the Darzens Reagent

In Situ Generation Technology of β-Butoxycarbonyliodonium Ylide: A Hypervalent Analogue of the Darzens Reagent
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β-丁氧基羰基碘叶立德的原位生成技术:Darzens 试剂的高价类似物

DOI:
10.1002/ejoc.201300413
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发表时间:
2013
期刊:
Eur. J. Org. Chem.
影响因子:
--
通讯作者:
Ochiai M.
Ochiai M.
中科院分区:
--
文献类型:
--
作者:
Miyamoto K.;Suzuki M.;Suefuji T.;Ochiai M.

文献摘要

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β-丁氧基-β-酰氧基乙烯基3-碘烷与锂碱(ROLi和nBuLi)的酯交换反应在低温下有效地生成了高度不稳定的单酯碘叶立德。原位生成的碘叶立德干净地与芳香醛发生Darzens缩合反应,选择性地生成反环氧酯。
An ester exchange reaction of β‐butoxy‐β‐acyloxyvinyl‐λ3‐iodane with lithium bases (ROLi andnBuLi) efficiently generates highly labile monoester iodonium ylide at low temperature. The iodonium ylide generated in situ cleanly undergoes Darzens condensation with aromatic aldehydes to affordtrans‐epoxy ester selectively.