Regio‐ and Stereoselective Stevens Rearrangement of Benzyltetrahydroprotoberberinium Salts | Zendy

Valpuesta Maria | Zendy; Diaz Amelia | Zendy; Suau Rafael | Zendy; Torres Gregorio | Zendy

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Regio‐ and Stereoselective Stevens Rearrangement of Benzyltetrahydroprotoberberinium Salts

Author(s) -

Valpuesta Maria,

Diaz Amelia,

Suau Rafael,

Torres Gregorio

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400443

Subject(s) - chemistry , stereoselectivity , competition (biology) , sodium salt , medicinal chemistry , stereochemistry , organic chemistry , catalysis , inorganic chemistry , ecology , biology

8‐(Arylmethyl)berbines are conveniently obtained through a Stevens rearrangement of the corresponding N ‐arylmethylberbinium salts with sodium methylsulfinylmethylide in DMSO. This procedure has provided two new nonnatural 8‐benzylcanadines stereoselectively, without competition from the Hofmann elimination. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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