Tetrahedron Asymmetry p. 1391 - 1404 (1996)
Update date:2022-08-11
Topics:
Bauer, Tomasz
Chapuis, Christian
Jezewski, Artur
Kozak, Janusz
Jurczak, Janusz
The chiral heterodienophile N-glyoxyloyl-(2R)-bornane-10,2-sultam 2, readily prepared from (2R)-bornane-10,2-sultam 1, was used in noncatalyzed atmospheric and high-pressure as well as in [Eu(fod)3]-catalyzed [4+2] cycloadditions with 1-methoxybuta-1,3-diene 3. All the [4+2] cycloadditions studied led to diastereoisomeric mixtures of 6-substituted derivatives of 2-methoxy-5,6-dihydro-2H-pyran 4-7. The extent of asymmetric induction in these reactions was established by 1H NMR analysis and the absolute configuration of the thermodynamically stable products 5 and 7 by X-ray analysis, and independently by chemical correlation. Stereochemical models for both noncatalyzed and [Eu(fod3]-promoted reactions are proposed. The [4+2] cycloadduct 5 was then effectively transformed into (4R)-hydroxy-(6S)-hydroxymethyltetrahydropyrone-2 12, a key synthon for the lactone moiety of compactin 10 and mevinolin 11.
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(1982)