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Synfacts 2022; 18(03): 0271
DOI: 10.1055/s-0041-1737854
Metals in Synthesis

Access to Oxazaborolidines by Catalytic Cycloaddition of 1,2-Azaborines and Vinyl Ethylene Carbonate

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Lucie Finck
Morita T, Murakami H, Asawa Y, Nakamura H. * Tokyo Institute of Technology, Yokohama, Japan
Enantioselective Synthesis of Oxazaborolidines by Palladium-Catalyzed N−H/B−H Double Activation of 1,2-Azaborines.

Angew. Chem. Int. Ed. 2022;
61
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Key words

asymmetric synthesis - 1,2-azaborines - cycloaddition - oxazaborolidines - palladium catalysis - vinylethylene carbonates

Significance

A palladium-catalyzed protocol for the (asymmetric) construction of oxazaborolidines is reported. The transformation proceeds through a decarboxylative/dehydrogenative (3+2) cycloaddition of 1,2-azaborines and vinyl ethylene carbonate.


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Comment

This procedure provides access to polycyclic oxazaborolidines in good yields and excellent enantioselectivities. Mechanistic experiments support the release of molecular H2 from the zwitterionic intermediate A.


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Publication History

Article published online:
16 February 2022

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