1997
DOI: 10.1021/ja971342g
|View full text |Cite
|
Sign up to set email alerts
|

Abstract: Density functional calculations (Becke3LYP/6-31G(d)) on the (3 + 2) transition structures of osmium tetroxide mediated dihydroxylations of chiral allylic ethers show that the stereoselectivity is controlled by the “inside alkoxy effect” (Stork/Houk-Jäger model). In the special case of Z-disubstituted alkenes, 1,3-allylic strain (Kishi model) controls the stereoselectivity.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1
1
1

Citation Types

5
40
0
1

Year Published

2001
2001
2008
2008

Publication Types

Select...
7
1

Relationship

0
8

Authors

Journals

citations
Cited by 72 publications
(46 citation statements)
references
References 27 publications
5
40
0
1
Order By: Relevance
“…[283] This apparently general trend is in agreement with the Stork-Houk-Jäger "inside-alkoxy" model. [284][285][286] The examination of substrates that contain 1,2-disubstituted cyclopropanes revealed several interesting trends. For example, treatment of the 1,2-cis-disubstituted cyclopropane 425 with the Ru catalyst under standard conditions produced exclusively the diastereomer 426 [Eq.…”
Section: Ruthenium-catalyzed [5+2] Cycloadditionmentioning
confidence: 99%
“…[283] This apparently general trend is in agreement with the Stork-Houk-Jäger "inside-alkoxy" model. [284][285][286] The examination of substrates that contain 1,2-disubstituted cyclopropanes revealed several interesting trends. For example, treatment of the 1,2-cis-disubstituted cyclopropane 425 with the Ru catalyst under standard conditions produced exclusively the diastereomer 426 [Eq.…”
Section: Ruthenium-catalyzed [5+2] Cycloadditionmentioning
confidence: 99%
“…Other recent support for the [3+2] mechanism has come from available experimental data [15] and new measurements of kinetic isotope effects [14,16] . Several stereoselective reactions have also been reported by Corey [15] , Houk [17] , Sharpless [18] , Haller [19] , and coworkers. To our knowledge, there have been only a few reports that styrene was catalyzed by (DHQD) 2 PYDZ·OsO 4 through theoretical calculations [20,21] .…”
Section: Introductionmentioning
confidence: 58%
“…This model, but not the Kishi model 122 However, a computational study 124 shows that the Kishi model controls the stereoselectivity for (Z)-alkenes. The rationale suggested by Houk et al is the following.…”
Section: The Inside Alkoxy Effectmentioning
confidence: 98%