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Practical Asymmetric Diels ‐ Alder Additions to Camphor‐10‐sulfonic‐Acid‐Derived Acrylates. Preliminary Communication
Author(s) -
Oppolzer Wolfgang,
Chapuis Christian,
Kelly Martha J.
Publication year - 1983
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.19830660747
Subject(s) - chemistry , camphor , adduct , cyclopentadiene , sulfonic acid , recrystallization (geology) , enantiopure drug , lewis acids and bases , organic chemistry , bridged compounds , acrylate , polymer chemistry , medicinal chemistry , enantioselective synthesis , polymer , catalysis , copolymer , paleontology , biology
Starting from (+)‐camphor‐10‐sulfonic acid (1) the chiral crystalline alcohols 3 and 11 were prepared in two steps. Lewis ‐acid‐mediated [4+2]‐additions of their acrylates to 1,3‐dienes were studied. Notably, the crystalline acrylate 4 underwent TiCl 2 (OiPr) 2 ‐promoted Diels ‐ Alder addition to cyclopentadiene giving after recrystallization efficiently the pure (2 R )‐adduct 5 .