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A Cross‐Metathesis–Conjugate Addition Route to Enantiopure γ‐Butyrolactams and γ‐Lactones from a C 2 ‐Symmetric Precursor
Author(s) -
Schmidt Bernd,
Staude Lucia,
Kelling Alexandra,
Schilde Uwe
Publication year - 2011
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.201001528
Subject(s) - chemistry , metathesis , enantiopure drug , conjugate , stereoselectivity , derivative (finance) , stereochemistry , ring closing metathesis , salt metathesis reaction , block (permutation group theory) , diene , methyl acrylate , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , combinatorics , copolymer , polymer , polymerization , financial economics , mathematical analysis , mathematics , economics , natural rubber
A protected derivative of (3 R ,4 R )‐hexa‐1,5‐diene‐3,4‐diol, a conveniently accessible C 2 ‐symmetric building block, undergoes single or double cross metathesis with methyl acrylate. The cross metathesis products are amenable to stereoselective conjugate addition reactions and can be converted into either γ‐butyrolactones or γ‐lactams.