Lewis Acid‐Catalyzed Stereoselective α‐Addition of Chiral Aldehydes to Cyclic Dienol Silanes: Aqueous Synthesis of Chiral Butenolides
The stereoselective α‐addition to cyclic dienol silanes has rarely been exploited, in contrast to the well‐studied γ‐addition of conjugated butenolides. In this study, an unprecedent catalytic Mukaiyama aldol α‐addition of 2‐trimetylsiloxy furan to optically pure aldehydes in water‐containing solven...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2020-02, Vol.362 (3), p.667-678 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Adamkiewicz, Anna Węglarz, Izabela Butkiewicz, Aleksandra Woyciechowska, Marta Mlynarski, Jacek |
| description | The stereoselective α‐addition to cyclic dienol silanes has rarely been exploited, in contrast to the well‐studied γ‐addition of conjugated butenolides. In this study, an unprecedent catalytic Mukaiyama aldol α‐addition of 2‐trimetylsiloxy furan to optically pure aldehydes in water‐containing solvents is reported. The synthetic utility of this concept was demonstrated in the efficient synthesis of six bioactive natural products: vitexolide D, curcucomosin C, villosin, chinensine C, (+)‐coronarin E and (E)‐labda‐7,11,13‐trien‐16,15‐olid. |
| doi_str_mv | 10.1002/adsc.201901218 |
| format | Article |
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| subjects | Aldehydes Diastereoselectivity Labdane diterpenes Lewis acid Mukaiyama aldol reaction Natural products Silanes Stereoselectivity Synthesis α-Regioselectivity |
| title | Lewis Acid‐Catalyzed Stereoselective α‐Addition of Chiral Aldehydes to Cyclic Dienol Silanes: Aqueous Synthesis of Chiral Butenolides |
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