Showing papers by "Yoshinobu Inouye published in 1990"
TL;DR: The acyliminium intermediate derived from (3R, 4R)-N-(3-butenyl)-3, 4-bis(benzyloxy)succinimide cyclized to give (8aS)- and (8 aR)-hexahydro-3(2H)-indolidinone derivatives as discussed by the authors.
Abstract: The acyliminium intermediate derived from (3R,4R)-N-(3-butenyl)-3,4-bis(benzyloxy)succinimide cyclized to give (8aS)- and (8aR)-hexahydro-3(2H)-indolidinone derivatives On the other hand, those derived from N-3-hexenyl derivatives afforded (8aS)-hexahydro-3(2H)-indolidinone(s) exclusively The geometry of the double bond reflected the stereochemistry of the products
13 citations
TL;DR: In this paper, the 1,3-dipolar cycloaddition of nitrile oxides to 2-X-bicyclo[2.2] oct-5-enes (X=O, NMe, S, SO2) was investigated together with acyclic and alicyclic analogues.
Abstract: The 1,3-dipolar cycloaddition of nitrile oxides to 2-X-bicyclo[2.2.2]oct-5-enes (X=O, NMe, S, SO2) were investigated together with acyclic and alicyclic analogues. The regioselectivity in an exo-attack was controlled by the heteroatom present at an allylic position —a remote attack was predominant in the cases of O and SO2 but a vicinal attack in those of NMe and S— and the results were rationalized from the electronic nature of the heteroatom, X. In an endo-attack, a remote attack was observed in every case and the dipole-dipole repulsion between X and the oxygen of the nitrile oxide was considered to be a predominant factor. The steric environment around the heteroatom controled the facial-selectivity.
7 citations
TL;DR: In this paper, the exact configuration of sipholenol-A was established by a single crystal X-ray analysis of its (S)-(−)-MTPA ester, which was recognized as an occupancy of 0.5:0.5 in crystalline state.
Abstract: Absolute configuration of sipholenol-A was established as (4S) by a single crystal X-ray analysis of its (S)-(−)-MTPA ester. Two conformers of the MTPA ester moiety were recognized as an occupancy of 0.5:0.5 in crystalline state; the positions of the groups can be rationalized by van der Waals interactions to nearest molecules.
5 citations
TL;DR: Three bicyclic olefins having an allylic oxygen atom (see title) were prepared and only 2-oxabicyclo[2.2]oct-5-ene could not be isolated in its pure state due to the volatility of the compound as discussed by the authors.
Abstract: Three bicyclic olefins having an allylic oxygen atom (see title) were prepared. Of those, 2-oxabicyclo[2.2.2]oct-5-ene could not be isolated in its pure state due to the volatility of the compound. The other two, however, could be isolated.
2 citations
TL;DR: Three bicyclic olefins having an allylic oxygen atom (see title) were prepared and only 2-oxabicyclo[2.2]oct-5-ene could not be isolated in its pure state due to the volatility of the compound as discussed by the authors.
Abstract: Three bicyclic olefins having an allylic oxygen atom (see title) were prepared. Of those, 2-oxabicyclo[2.2.2]oct-5-ene could not be isolated in its pure state due to the volatility of the compound. The other two, however, could be isolated.
TL;DR: The acyliminium intermediate derived from (3R, 4R)-N-(3-butenyl)-3, 4-bis(benzyloxy)succinimide cyclized to give (8aS)- and (8 aR)-hexahydro-3(2H)-indolidinone derivatives as mentioned in this paper.
Abstract: The acyliminium intermediate derived from (3R,4R)-N-(3-butenyl)-3,4-bis(benzyloxy)succinimide cyclized to give (8aS)- and (8aR)-hexahydro-3(2H)-indolidinone derivatives. On the other hand, those derived from N-3-hexenyl derivatives afforded (8aS)-hexahydro-3(2H)-indolidinone(s) exclusively. The geometry of the double bond reflected the stereochemistry of the products.