Scope and Limitations of the Domino Vinylogous Aldol/oxa‐Michael Reaction
Scope and Limitations of the Domino Vinylogous Aldol/oxa‐Michael Reaction
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DOI：
10.1002/slct.201700667
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发表时间：
2017-04
期刊：
影响因子：
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通讯作者：
Larissa Geiger;M. Nieger;Stefan Bräse
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文献类型：
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作者：
Larissa Geiger;M. Nieger;Stefan Bräse
在有机催化剂存在下，水杨醛与α，β-不饱和醛的不对称、原子经济反应导致手性三环色满。在这份报告中，杂原子取代的α，β-不饱和醛的第一次探索证明：我们提出了对映选择性多米诺乙烯基羟醛/oxa-Michael反应的范围和限制方面的调查。来自该反应的手性色满是高度官能化的，并且是通用的合成中间体，其可以进一步转化为在C-4a位置上具有官能度的相应四氢氧杂蒽酮。从对甲氧基苯基保护的醇开始，开发了在该位置上的甲酯的新合成路线。
The asymmetric, atom economic reaction of salicylaldehydes withα,β‐unsaturated aldehydes in the presence of an organocatalyst leads to chiral tricyclic chromanes. In this report, the first exploration of heteroatom‐substitutedα,β‐unsaturated aldehydes is demonstrated: We present the investigation of the enantioselective domino vinylogous aldol/oxa‐Michael reaction in respect to its scope and limitations. The chiral chromanes arriving from this reaction are highly functionalized and are versatile synthetic intermediates that can further be converted into the respective tetrahydroxanthones with functionalities on the C‐4a position. A new synthetic route to a methyl ester on this position is developed starting with ap‐methoxyphenyl protected alcohol.