A new design for chiral induction: a highly regioselective differentiation between two identical groups in an acyclic compound having a prochiral center

1982 ◽  
Vol 104 (7) ◽  
pp. 2079-2081 ◽  
Author(s):  
Yoshimitsu Nagao ◽  
Takao Ikeda ◽  
Masahiro Yagi ◽  
Eiichi Fujita ◽  
Motoo Shiro



Synfacts ◽  
2010 ◽  
Vol 2011 (01) ◽  
pp. 0105-0105
Author(s):  
C. Duan ◽  
D. Dang ◽  
P. Wu ◽  
C. He ◽  
Z. Xie


Tetrahedron ◽  
1984 ◽  
Vol 40 (8) ◽  
pp. 1215-1223 ◽  
Author(s):  
Yoshimitsu nagao ◽  
Takemsa inoue ◽  
Eiichi fujita ◽  
Shunji Terada ◽  
Motoo shiro
Keyword(s):  




2017 ◽  
Vol 244 ◽  
pp. 398-404 ◽  
Author(s):  
V.A. Burmistrov ◽  
I.V. Novikov ◽  
V.V. Aleksandriiskii ◽  
M.K. Islyaikin ◽  
O.I. Koifman


1997 ◽  
Vol 75 (7) ◽  
pp. 1030-1040 ◽  
Author(s):  
T.S. Sorensen ◽  
F. Sun

The preparation of the strained cis-2,3-di-tert-butylcyclopropanone 2 from the acyclic compound, α,α′-dibromodineopentyl ketone 1, using a previously reported methodology, is dramatic evidence of both the existence of oxyallyl intermediates in the mechanism of this reaction, and of the integrity with which oxyallyls ring-close to cyclopropanones by a disrotatory route. Because of the bulky cis substituents, cyclopropanone 2 exhibits a number of unusual spectroscopic features (as compared to the trans isomer 5). With the aid of ab initio calculations on 2 and 5, it can be shown that the C2—C3 bond in 2 interacts with the carbonyl π-orbitals, thus causing the carbonyl oxygen to bend 12° out of the plane; this interaction is absent in 5 and the latter has a planar carbonyl group. As with other cyclopropanones, 2 can be photochemically decarbonylated. This process itself appears to be stereospecific even though highly strained alkenes are produced. Cyclopropanone 2 is thermally rearranged to the trans isomer 5 and the kinetics for this are reported; our favoured mechanism involves oxyallyl intermediates. Other reactions of 2 also appear to proceed through these oxyallyl species; for example, alcohols initially add to 2 to give α-alkoxy ends, solutions of 2 enter into very facile diene cycloadditions, and the dimerization of neat 2 also appears to involve these oxyallyl species. Keywords: cyclopropanones, oxyallyl, stereomutation, stereospecific decarbonylation, nonplanar carbonyl.



2010 ◽  
Vol 58 (6) ◽  
pp. 872-874 ◽  
Author(s):  
Hiroaki Saito ◽  
Ryo Iwai ◽  
Taketo Uchiyama ◽  
Muneharu Miyake ◽  
Shinichi Miyairi


2002 ◽  
Vol 337 (7) ◽  
pp. 651-656 ◽  
Author(s):  
Cristina De Castro ◽  
Antonio Molinaro ◽  
Federico Giordano ◽  
Ida Orabona ◽  
Francesco Ruffo


2004 ◽  
Vol 14 (6) ◽  
pp. 256-257 ◽  
Author(s):  
David B. Amabilino ◽  
José-Luis Serrano ◽  
Teresa Sierra ◽  
Jaume Veciana
Keyword(s):  


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