Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters

Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters

In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon...

Full description

Saved in:
Bibliographic Details
Main Authors: Yan, Lin, Han, Zhiqiang, Zhu, Bo, Yang, Caiyun, Tan, Choon-Hong, Jiang, Zhiyong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2013
Subjects:
DRNTU::Science::Chemistry::Organic chemistry
Online Access:https://hdl.handle.net/10356/99329
http://hdl.handle.net/10220/17425
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Nanyang Technological University
Language: English
id sg-ntu-dr.10356-99329
record_format dspace
spelling sg-ntu-dr.10356-993292023-02-28T19:36:57Z Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters Yan, Lin Han, Zhiqiang Zhu, Bo Yang, Caiyun Tan, Choon-Hong Jiang, Zhiyong School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr). Published Version 2013-11-08T02:32:46Z 2019-12-06T20:06:03Z 2013-11-08T02:32:46Z 2019-12-06T20:06:03Z 2013 2013 Journal Article Yan, L., Han, Z., Zhu, B., Yang, C., Tan, C.-H., & Jiang, Z. (2013). Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters. Beilstein journal of organic chemistry, 9, 1853-1857. https://hdl.handle.net/10356/99329 http://hdl.handle.net/10220/17425 10.3762/bjoc.9.216 24062852 en Beilstein journal of organic chemistry © 2013 Yan et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions:(http://www.beilstein-journals.org/bjoc) application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry
spellingShingle DRNTU::Science::Chemistry::Organic chemistry
Yan, Lin
Han, Zhiqiang
Zhu, Bo
Yang, Caiyun
Tan, Choon-Hong
Jiang, Zhiyong
Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters
description In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr).
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Yan, Lin
Han, Zhiqiang
Zhu, Bo
Yang, Caiyun
Tan, Choon-Hong
Jiang, Zhiyong
format Article
author Yan, Lin
Han, Zhiqiang
Zhu, Bo
Yang, Caiyun
Tan, Choon-Hong
Jiang, Zhiyong
author_sort Yan, Lin
title Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters
title_short Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters
title_full Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters
title_fullStr Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters
title_full_unstemmed Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters
title_sort asymmetric allylic alkylation of morita–baylis–hillman carbonates with α-fluoro-β-keto esters
publishDate 2013
url https://hdl.handle.net/10356/99329
http://hdl.handle.net/10220/17425
_version_ 1759857604471816192

Similar Items