2016
DOI: 10.3762/bjoc.12.255
|View full text |Cite
|
Sign up to set email alerts
|

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

Abstract: Synthesis of novel polyhydroxylated derivatives of decalin is described. The presented methodology consists in a one-pot copper-catalyzed 1,4-addition of vinylmagnesium bromide to sugar-derived cyclohexenone, followed by an aldol reaction with a derivative of but-3-enal. The obtained diene is then subjected to an assisted tandem catalytic sequence: ring-closing metathesis with the subsequent reuse of the Ru-catalyst in the syn-dihydroxylation. The stereochemical outcome of these reactions is discussed.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1

Citation Types

0
1
0

Year Published

2017
2017
2022
2022

Publication Types

Select...
5

Relationship

0
5

Authors

Journals

citations
Cited by 5 publications
(1 citation statement)
references
References 55 publications
0
1
0
Order By: Relevance
“…A year later the same author reported the synthesis of optically pure polyhydroxylated trans ‐decalins 5–6 through a sequence of a one‐pot 1,4‐addition/aldol reaction and RCM/ syn ‐dihydroxylation (Scheme 6a–b). [ 26 ] Desired syn ‐diols were obtained, from two different diastereomers, with moderate overall yield but with good to high diastereoselectivity respectively. To explain the observed high selectivity the author suggested that the syn‐ dihydroxylation proceeded from the less congested face of the double bond ( anti compared to the neighboring benzoyl group, see Scheme 6c).…”
Section: Ruthenium‐mediated Syn‐dihydroxylationmentioning
confidence: 99%
“…A year later the same author reported the synthesis of optically pure polyhydroxylated trans ‐decalins 5–6 through a sequence of a one‐pot 1,4‐addition/aldol reaction and RCM/ syn ‐dihydroxylation (Scheme 6a–b). [ 26 ] Desired syn ‐diols were obtained, from two different diastereomers, with moderate overall yield but with good to high diastereoselectivity respectively. To explain the observed high selectivity the author suggested that the syn‐ dihydroxylation proceeded from the less congested face of the double bond ( anti compared to the neighboring benzoyl group, see Scheme 6c).…”
Section: Ruthenium‐mediated Syn‐dihydroxylationmentioning
confidence: 99%