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Asymmetric Diels ‐ Alder Reaction of 1‐Methoxybuta‐1,3‐diene with (2 R )‐ N ‐Glyoxyloylbornane‐10,2‐sultam
Author(s) -
Bauer Tomasz,
Chapuis Christian,
Kozak Janusz,
Jurczak Janusz
Publication year - 1989
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.19890720310
Subject(s) - chemistry , diene , asymmetric induction , pyran , diels–alder reaction , catalysis , medicinal chemistry , atmospheric pressure , stereochemistry , organic chemistry , computational chemistry , enantioselective synthesis , natural rubber , oceanography , geology
Starting from sultam 1 , the chiral dienophile (2 R )‐ N ‐glyoxyloylbornane‐10,2‐sultam ( 4 ) was readily prepared. Non‐catalyzed atmospheric‐ and high‐pressure as well as [Eu(fod) 3 ]‐promoted [4 + 2] cycloadditions of 1‐methoxy‐buta‐1,3‐diene ( 5 ) to chiral dienophile 4 , leading with high asymmetric induction to 6‐methoxy‐3,6‐dihydro‐2 H ‐pyran‐2‐yl derivatives 6 – 9 , are described. The extent and direction of asymmetric induction in these reactions were established by 1 H‐NMR analysis and chemical correlation, respectively. Stereochemical models for both non‐catalyzed and [Eu(fod) 3 ]‐promoted reactions are proposed.