Stereoselective Synthesis of 1,4-Diols by a Tandem Allylboration–Allenylboration Sequence | Zendy

Tony S. N. Zhao | Zendy; Jian Zhao | Zendy; Kálmán J. Szabó | Zendy

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Stereoselective Synthesis of 1,4-Diols by a Tandem Allylboration–Allenylboration Sequence

Author(s) -

Tony S. N. Zhao,

Jian Zhao,

Kálmán J. Szabó

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b01048

Subject(s) - stereocenter , chemistry , stereoselectivity , aldehyde , tandem , sequence (biology) , substrate (aquarium) , chirality (physics) , cascade reaction , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry , materials science , oceanography , physics , quantum mechanics , quark , geology , nambu–jona lasinio model , composite material , chiral symmetry breaking

The reaction of mono- and dialdehydes with bis-borodienes (incorporating an allylboronate unit) has been studied. It was found that the initial allylboration reaction results in an allenylboronate, which has two stereogenic units: one of them has axial chirality and the other one is a stereogenic carbon center. This reaction proceeds with high diastereoselectivity. The allenylboronate formed in the allylboration reacts with an additional aldehyde with fair to high stereoselectivity depending on the aldehyde substrate. Aromatic dialdehydes react with bis-boro-butadienes creating three new stereocenters with usually high diastereoselectivity.

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