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A multicomponent approach for the preparation of homoallylic alcohols † † Raw spectra can be found at DOI: 10.17863/CAM.591 ‡ ‡ Electronic supplementary information (ESI) available. CCDC 1483699 . For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc02581a Click here for additional data file. Click here for additional data file.

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ABSTRACT

Here we report the in situ generation of transient allylic boronic species, by reacting TMSCHN2 and E-vinyl boronic acids, followed by their subsequent trapping with aldehydes as electrophiles to yield homoallylic alcohols. This metal-free reaction was initially discovered by the use of a flow chemistry approach to generate a variety of homoallylic alcohols in a straightforward fashion and then transferred to a batch protocol.

No MeSH data available.


Iterative process to polyol 8 and tetrahydropyran derivative 9.
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sch2: Iterative process to polyol 8 and tetrahydropyran derivative 9.

Mentions: Wishing to broaden the practical aspect of this multicomponent metal-free reaction, we decided to transfer the method directly into a batch process (Scheme 2), having taken care to safely handle the TMSCHN2 reagent. The optimised batch protocol was developed at room temperature with reaction times being within the range from 2 h to 16 h for similar reaction scale (0.3 mmol). The scope of the reaction under batch conditions was expanded and demonstrated the generality of the method (Table 2).


A multicomponent approach for the preparation of homoallylic alcohols † † Raw spectra can be found at DOI: 10.17863/CAM.591 ‡ ‡ Electronic supplementary information (ESI) available. CCDC 1483699 . For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc02581a Click here for additional data file. Click here for additional data file.
Iterative process to polyol 8 and tetrahydropyran derivative 9.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5134730&req=5

sch2: Iterative process to polyol 8 and tetrahydropyran derivative 9.
Mentions: Wishing to broaden the practical aspect of this multicomponent metal-free reaction, we decided to transfer the method directly into a batch process (Scheme 2), having taken care to safely handle the TMSCHN2 reagent. The optimised batch protocol was developed at room temperature with reaction times being within the range from 2 h to 16 h for similar reaction scale (0.3 mmol). The scope of the reaction under batch conditions was expanded and demonstrated the generality of the method (Table 2).

View Article: PubMed Central - PubMed

ABSTRACT

Here we report the in situ generation of transient allylic boronic species, by reacting TMSCHN2 and E-vinyl boronic acids, followed by their subsequent trapping with aldehydes as electrophiles to yield homoallylic alcohols. This metal-free reaction was initially discovered by the use of a flow chemistry approach to generate a variety of homoallylic alcohols in a straightforward fashion and then transferred to a batch protocol.

No MeSH data available.