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A facile and mild synthesis of trisubstituted allylic sulfones from Morita-Baylis-Hillman carbonates.


ABSTRACT: An efficient and catalyst-free synthesis of trisubstituted allylic sulfones through an allylic sulfonylation reaction of Morita-Baylis-Hillman (MBH) carbonates with sodium sulfinates has been developed. Under the optimized reaction conditions, a series of trisubstituted allylic sulfones were rapidly prepared in good to excellent yields (71%-99%) with good to high selectivity (Z/E from 79:21 to >99:1). Compared with known synthetic methods, the current protocol features mild reaction temperature, high efficiency and easily available reagents.

SUBMITTER: Jiang L 

PROVIDER: S-EPMC6272667 | biostudies-other | 2015 May

REPOSITORIES: biostudies-other

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A facile and mild synthesis of trisubstituted allylic sulfones from Morita-Baylis-Hillman carbonates.

Jiang Lin L   Li Yong-Gen YG   Zhou Jiang-Feng JF   Chuan Yong-Ming YM   Li Hong-Li HL   Yuan Ming-Long ML  

Molecules (Basel, Switzerland) 20150507 5


An efficient and catalyst-free synthesis of trisubstituted allylic sulfones through an allylic sulfonylation reaction of Morita-Baylis-Hillman (MBH) carbonates with sodium sulfinates has been developed. Under the optimized reaction conditions, a series of trisubstituted allylic sulfones were rapidly prepared in good to excellent yields (71%-99%) with good to high selectivity (Z/E from 79:21 to >99:1). Compared with known synthetic methods, the current protocol features mild reaction temperature,  ...[more]

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