Tetrahedron Asymmetry p. 2319 - 2328 (1995)
Update date:2022-08-11
Topics:
Marotta
Pagani
Righi
Rosini
Bertolasi
Medici
Single crystal X-ray diffraction analysis of compounds A, B and C helped us to assign the absolute configurations of the enantiomers of the bicyclo[3.2.0]hept-3-en-6-endo-ols 4-6. These bicyclic alcohols were easily obtained by: (i) stereoselective reductions of the bicyclo[3.2.0]hept-3-en-6-ones 1-3, (ii) conversion into diastereoisomeric pairs using (-)-(1S,4R)-camphanic acid chloride as resolving agent, (iii) an efficient separation of diastereoisomers by flash-chromatography and, finally, (iv) a mild alkaline hydrolysis. The oxidation of pure enantiomers of the bicyclo[3.2.0]hept-3-en-6-endo-ols 4-6 with tetra-n-propylammonium perruthenate (TPAP) and N-methylmorpholine N-oxide (NMO) as co-oxidant furnished enantiomerically pure bicyclo[3.2.0]hept-3-en-6-ones 1-3. The different mutual disposition of carbonyl groups in the structure A and B justifies the different IR (KBr) signals for the carbonyls of each diastereoisomer.
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Doi:10.1021/ja01600a029
(1956)Doi:10.1021/acschembio.8b00266
(2018)Doi:10.1039/c4ra02700k
(2014)Doi:10.1021/ja00397a046
(1981)Doi:10.1515/chempap-2016-0083
(2016)Doi:10.1021/jo00835a062
(1970)