A One‐Pot Organometallic Route from a 4‐Alkenylpyridine to a 4,4‐Spiro‐Linked Ethyl 1,4‐Dihydropyridine‐1‐carboxylate | Zendy

Fraenkel Gideon | Zendy; Chow Albert | Zendy; Liang Yulan | Zendy; Song Jinhua | Zendy; Gallucci Judith | Zendy

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A One‐Pot Organometallic Route from a 4‐Alkenylpyridine to a 4,4‐Spiro‐Linked Ethyl 1,4‐Dihydropyridine‐1‐carboxylate

Author(s) -

Fraenkel Gideon,

Chow Albert,

Liang Yulan,

Song Jinhua,

Gallucci Judith

Publication year - 2012

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.201200373

Subject(s) - chemistry , carboxylate , pyridine , yield (engineering) , dihydropyridine , medicinal chemistry , stereochemistry , organic chemistry , calcium , materials science , metallurgy

In a one‐pot process without isolation of intermediates, (but‐3‐en‐1‐yl)pyridine ( 13 ) is treated sequentially with dicyclohexylborane, trimethylaluminium, and ethyl carbonochloridate yielding ethyl 1,4‐dihydro‐4,4‐(tetramethylene)pyridine‐1‐carboxylate (=ethyl 8‐azaspiro[4.5]deca‐6,9‐diene‐8‐carboxylate; 2 ) in 46% yield based on starting alkenylpyridine 13 ( Scheme 5 ).

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