Preparation and odour properties of the four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran
ABSTRACT The four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran were prepared starting from ( R )‐ or ( S )‐1‐decen‐4‐ol (>96% ee). They were obtained by kinetic resolution of racemic homoallylic alcohol catalysed by Novozym 435 ( Candida antarctica ). ( R )‐ or ( S )‐1‐Decen‐4‐ol proceeded S...
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crwiley:10.1002/ffj.3202 2024-06-02T07:57:20+00:00 Preparation and odour properties of the four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran Zhang, Guoying Gong, Xiuqin Yang, Shaoxiang Sun, Baoguo Liu, Yongguo Tian, Hongyu Financial support from the National Natural Science Foundation of China the Importation and Development of High-Caliber Talents Project of Beijing Municipal Institutions the National Key Technology R&D Program 2014 http://dx.doi.org/10.1002/ffj.3202 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fffj.3202 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ffj.3202 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Flavour and Fragrance Journal volume 29, issue 4, page 249-254 ISSN 0882-5734 1099-1026 journal-article 2014 crwiley https://doi.org/10.1002/ffj.3202 2024-05-03T11:34:16Z ABSTRACT The four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran were prepared starting from ( R )‐ or ( S )‐1‐decen‐4‐ol (>96% ee). They were obtained by kinetic resolution of racemic homoallylic alcohol catalysed by Novozym 435 ( Candida antarctica ). ( R )‐ or ( S )‐1‐Decen‐4‐ol proceeded Sharpless asymmetric dihydroxylation (AD) using AD‐mix‐α or β as an oxidant followed by ring closure to afford cis ‐2‐hexyl‐4‐hydroxytetrahydrofuran as the major product with 50–60% de. The diastereomers were separated by derivatization to the corresponding p ‐nitrobenzoates, and the ee values of cis ‐isomers were determined by chiral HPLC to be >96%. A pair of enantiomers of cis ‐2‐hexyl‐4‐hydroxytetrahydrofuran was produced by hydrolysis of the corresponding p ‐nitrobenzoate, respectively. The four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran were obtained with >95% ee values from (2 S ,4 R )‐ or (2 R ,4 S )‐ cis ‐2‐hexyl‐4‐hydroxytetrahydrofuran by direct acylation with acetic anhydride or Mitsunobu reaction with acetic acid in the presence of Ph 3 P and diisopropyl azodicarboxylate. The four stereoisomers presented very distinct differences in both feature and intensity. Copyright © 2014 John Wiley & Sons, Ltd. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Flavour and Fragrance Journal 29 4 249 254 |
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English |
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ABSTRACT The four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran were prepared starting from ( R )‐ or ( S )‐1‐decen‐4‐ol (>96% ee). They were obtained by kinetic resolution of racemic homoallylic alcohol catalysed by Novozym 435 ( Candida antarctica ). ( R )‐ or ( S )‐1‐Decen‐4‐ol proceeded Sharpless asymmetric dihydroxylation (AD) using AD‐mix‐α or β as an oxidant followed by ring closure to afford cis ‐2‐hexyl‐4‐hydroxytetrahydrofuran as the major product with 50–60% de. The diastereomers were separated by derivatization to the corresponding p ‐nitrobenzoates, and the ee values of cis ‐isomers were determined by chiral HPLC to be >96%. A pair of enantiomers of cis ‐2‐hexyl‐4‐hydroxytetrahydrofuran was produced by hydrolysis of the corresponding p ‐nitrobenzoate, respectively. The four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran were obtained with >95% ee values from (2 S ,4 R )‐ or (2 R ,4 S )‐ cis ‐2‐hexyl‐4‐hydroxytetrahydrofuran by direct acylation with acetic anhydride or Mitsunobu reaction with acetic acid in the presence of Ph 3 P and diisopropyl azodicarboxylate. The four stereoisomers presented very distinct differences in both feature and intensity. Copyright © 2014 John Wiley & Sons, Ltd. |
author2 |
Financial support from the National Natural Science Foundation of China the Importation and Development of High-Caliber Talents Project of Beijing Municipal Institutions the National Key Technology R&D Program |
format |
Article in Journal/Newspaper |
author |
Zhang, Guoying Gong, Xiuqin Yang, Shaoxiang Sun, Baoguo Liu, Yongguo Tian, Hongyu |
spellingShingle |
Zhang, Guoying Gong, Xiuqin Yang, Shaoxiang Sun, Baoguo Liu, Yongguo Tian, Hongyu Preparation and odour properties of the four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran |
author_facet |
Zhang, Guoying Gong, Xiuqin Yang, Shaoxiang Sun, Baoguo Liu, Yongguo Tian, Hongyu |
author_sort |
Zhang, Guoying |
title |
Preparation and odour properties of the four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran |
title_short |
Preparation and odour properties of the four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran |
title_full |
Preparation and odour properties of the four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran |
title_fullStr |
Preparation and odour properties of the four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran |
title_full_unstemmed |
Preparation and odour properties of the four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran |
title_sort |
preparation and odour properties of the four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran |
publisher |
Wiley |
publishDate |
2014 |
url |
http://dx.doi.org/10.1002/ffj.3202 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fffj.3202 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ffj.3202 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Flavour and Fragrance Journal volume 29, issue 4, page 249-254 ISSN 0882-5734 1099-1026 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/ffj.3202 |
container_title |
Flavour and Fragrance Journal |
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29 |
container_issue |
4 |
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249 |
op_container_end_page |
254 |
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1800740485418975232 |