Predict the product from the reactionPredict the product (organic chemistry)Predict the Product(s) of a...
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Predict the product from the reaction
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Predict the product from the reaction
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Not exactly sure what kind of reaction this is. But here's my attempt. LDA is a strong base and probably deprotonates somewhere which I'm not sure about. It I would to make a guess it would probably be beta to the imine. This is following by nucleophilic attack of the carboanion onto the use of the second reagent Pr-CHO to generate an alcohol. But I'm not sure the purpose of the 3rd reagent (oxalic acid).
organic-chemistry reaction-mechanism
asked 10 hours ago
derrickderrick
1013
$endgroup$
add a comment |
$begingroup$
Not exactly sure what kind of reaction this is. But here's my attempt. LDA is a strong base and probably deprotonates somewhere which I'm not sure about. It I would to make a guess it would probably be beta to the imine. This is following by nucleophilic attack of the carboanion onto the use of the second reagent Pr-CHO to generate an alcohol. But I'm not sure the purpose of the 3rd reagent (oxalic acid).
organic-chemistry reaction-mechanism
asked 10 hours ago
derrickderrick
1013
$endgroup$
add a comment |
$begingroup$
Not exactly sure what kind of reaction this is. But here's my attempt. LDA is a strong base and probably deprotonates somewhere which I'm not sure about. It I would to make a guess it would probably be beta to the imine. This is following by nucleophilic attack of the carboanion onto the use of the second reagent Pr-CHO to generate an alcohol. But I'm not sure the purpose of the 3rd reagent (oxalic acid).
organic-chemistry reaction-mechanism
asked 10 hours ago
derrickderrick
1013
$endgroup$
Not exactly sure what kind of reaction this is. But here's my attempt. LDA is a strong base and probably deprotonates somewhere which I'm not sure about. It I would to make a guess it would probably be beta to the imine. This is following by nucleophilic attack of the carboanion onto the use of the second reagent Pr-CHO to generate an alcohol. But I'm not sure the purpose of the 3rd reagent (oxalic acid).
organic-chemistry reaction-mechanism
organic-chemistry reaction-mechanism
asked 10 hours ago
derrickderrick
1013
asked 10 hours ago
derrickderrick
1013
edited 10 hours ago
derrick
asked 10 hours ago
derrickderrick
1013
asked 10 hours ago
derrickderrick
1013
asked 10 hours ago
derrickderrick
1013
1013
add a comment |
add a comment |
2 Answers
2
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oldest
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$begingroup$
This is a Peterson olefination, specifically this one is from the synthesis of Roseophilin published in J. Am. Chem. Soc. (2001) 123 8509. The LDA deprotonates next to the silicon as both it and the adjacent imine stabilise the anion.
The Wikipedia page gives a good summary of the mechanism and why an acidic work up is used in this case to give the required double bond geometry (Wikipedia).
(Image from www.chem.wisc.edu)
answered 10 hours ago
WaylanderWaylander
7,77211726
$endgroup$
add a comment |
$begingroup$
@ Waylander has nailed it.
But , an interesting part of mechanism is,it proceeds via chair form of six membred transition state as shown here. Among two possible transition states , only one is favored.The other transition state, disfavored has isopropyl group(from LDA) and trimethylsilyl group in axial positions leading to 1,3 diaxial repulsions(shown in the figure below).
source
In this mechanism,the starting material is an ester.You could use starting material in the post instead.
answered 9 hours ago
Chakravarthy KalyanChakravarthy Kalyan
1,941422
$endgroup$
add a comment |
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2 Answers
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2 Answers
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$begingroup$
This is a Peterson olefination, specifically this one is from the synthesis of Roseophilin published in J. Am. Chem. Soc. (2001) 123 8509. The LDA deprotonates next to the silicon as both it and the adjacent imine stabilise the anion.
The Wikipedia page gives a good summary of the mechanism and why an acidic work up is used in this case to give the required double bond geometry (Wikipedia).
(Image from www.chem.wisc.edu)
answered 10 hours ago
WaylanderWaylander
7,77211726
$endgroup$
add a comment |
$begingroup$
This is a Peterson olefination, specifically this one is from the synthesis of Roseophilin published in J. Am. Chem. Soc. (2001) 123 8509. The LDA deprotonates next to the silicon as both it and the adjacent imine stabilise the anion.
The Wikipedia page gives a good summary of the mechanism and why an acidic work up is used in this case to give the required double bond geometry (Wikipedia).
(Image from www.chem.wisc.edu)
answered 10 hours ago
WaylanderWaylander
7,77211726
$endgroup$
add a comment |
$begingroup$
This is a Peterson olefination, specifically this one is from the synthesis of Roseophilin published in J. Am. Chem. Soc. (2001) 123 8509. The LDA deprotonates next to the silicon as both it and the adjacent imine stabilise the anion.
The Wikipedia page gives a good summary of the mechanism and why an acidic work up is used in this case to give the required double bond geometry (Wikipedia).
(Image from www.chem.wisc.edu)
answered 10 hours ago
WaylanderWaylander
7,77211726
$endgroup$
This is a Peterson olefination, specifically this one is from the synthesis of Roseophilin published in J. Am. Chem. Soc. (2001) 123 8509. The LDA deprotonates next to the silicon as both it and the adjacent imine stabilise the anion.
The Wikipedia page gives a good summary of the mechanism and why an acidic work up is used in this case to give the required double bond geometry (Wikipedia).
(Image from www.chem.wisc.edu)
answered 10 hours ago
WaylanderWaylander
7,77211726
edited 10 hours ago
answered 10 hours ago
WaylanderWaylander
7,77211726
answered 10 hours ago
WaylanderWaylander
7,77211726
answered 10 hours ago
WaylanderWaylander
7,77211726
7,77211726
add a comment |
add a comment |
$begingroup$
@ Waylander has nailed it.
But , an interesting part of mechanism is,it proceeds via chair form of six membred transition state as shown here. Among two possible transition states , only one is favored.The other transition state, disfavored has isopropyl group(from LDA) and trimethylsilyl group in axial positions leading to 1,3 diaxial repulsions(shown in the figure below).
source
In this mechanism,the starting material is an ester.You could use starting material in the post instead.
answered 9 hours ago
Chakravarthy KalyanChakravarthy Kalyan
1,941422
$endgroup$
add a comment |
$begingroup$
@ Waylander has nailed it.
But , an interesting part of mechanism is,it proceeds via chair form of six membred transition state as shown here. Among two possible transition states , only one is favored.The other transition state, disfavored has isopropyl group(from LDA) and trimethylsilyl group in axial positions leading to 1,3 diaxial repulsions(shown in the figure below).
source
In this mechanism,the starting material is an ester.You could use starting material in the post instead.
answered 9 hours ago
Chakravarthy KalyanChakravarthy Kalyan
1,941422
$endgroup$
add a comment |
$begingroup$
@ Waylander has nailed it.
But , an interesting part of mechanism is,it proceeds via chair form of six membred transition state as shown here. Among two possible transition states , only one is favored.The other transition state, disfavored has isopropyl group(from LDA) and trimethylsilyl group in axial positions leading to 1,3 diaxial repulsions(shown in the figure below).
source
In this mechanism,the starting material is an ester.You could use starting material in the post instead.
answered 9 hours ago
Chakravarthy KalyanChakravarthy Kalyan
1,941422
$endgroup$
@ Waylander has nailed it.
But , an interesting part of mechanism is,it proceeds via chair form of six membred transition state as shown here. Among two possible transition states , only one is favored.The other transition state, disfavored has isopropyl group(from LDA) and trimethylsilyl group in axial positions leading to 1,3 diaxial repulsions(shown in the figure below).
source
In this mechanism,the starting material is an ester.You could use starting material in the post instead.
answered 9 hours ago
Chakravarthy KalyanChakravarthy Kalyan
1,941422
answered 9 hours ago
Chakravarthy KalyanChakravarthy Kalyan
1,941422
answered 9 hours ago
Chakravarthy KalyanChakravarthy Kalyan
1,941422
answered 9 hours ago
Chakravarthy KalyanChakravarthy Kalyan
1,941422
1,941422
add a comment |
add a comment |
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