Catalytic asymmetric intramolecular Michael reaction of aldehydes

Catalytic asymmetric intramolecular Michael reaction of aldehydes
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DOI:
10.1002/anie.200460578
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发表时间:
2004-01-01
影响因子:
16.6
通讯作者:
List, B
List, B
中科院分区:
化学1区
文献类型:
--
作者:
Fonseca, MTH;List, B

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通过咪唑烷酮催化剂对甲酰基烯酮(例如1)的分子内迈克尔反应进行有效的有机催化,以优异的产率和高的对映选择性产生相应的酮醛(参见方案)。该反应可以作为串联方法的一部分,因为酮醛产物容易经历羟醛化以得到氢化茚酮,例如2。Bn=苄基,Ms=甲磺酰基。
Efficient organocatalysis of the intramolecular Michael reaction of formyl enones, such as 1, by an imidazolidinone catalyst leads to the corresponding ketoaldehydes in excellent yields and with high enantioselectivities (see scheme). This reaction can be included as part of a tandem process, as the ketoaldehyde products undergo aldolization readily to give hydrindenones, such as 2. Bn= benzyl, Ms= methanesulfonyl.