Practical Asymmetric  Diels ‐ Alder  Additions to Camphor‐10‐sulfonic‐Acid‐Derived Acrylates. Preliminary Communication | Zendy

Oppolzer Wolfgang | Zendy; Chapuis Christian | Zendy; Kelly Martha J. | Zendy

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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 .

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