Crown Ether‐Assisted Change of Regioselectivity in the Reductive Cleavage of Allylsulfonamides | Zendy

Moiseenkov Alexander M. | Zendy; Polunin Evgeni V. | Zendy; Semenovsky Alexei V. | Zendy

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Crown Ether‐Assisted Change of Regioselectivity in the Reductive Cleavage of Allylsulfonamides

Author(s) -

Moiseenkov Alexander M.,

Polunin Evgeni V.,

Semenovsky Alexei V.

Publication year - 1981

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198110571

Subject(s) - regioselectivity , nerol , chemistry , crown ether , ether , cleavage (geology) , organic chemistry , stereochemistry , geraniol , catalysis , chromatography , materials science , ion , fracture (geology) , composite material , essential oil

In order to use the hydroxysulfonamide (1) for the C 5 ‐homologation of isoprenoids it was necessary to regioselectively reduce allylsulfonamides such as (2) . If classical methods are used for this purpose a ca. 1:9 mixture of nerol (3) and isogeraniol (4) is formed; in contrast, (2) reacts with Na/NH 3 in the presence of dibenzo‐[18]crown‐6 to give almost exclusively (3) .

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