Asymmetric Conjugate Addition of Boronates to N-Acylimines and β-Silyl-α,β-unsaturated Ketones Catalyzed by 3,3'-Disubstituted Binaphthols

Asymmetric Conjugate Addition of Boronates to N-Acylimines and β-Silyl-α,β-unsaturated Ketones Catalyzed by 3,3'-Disubstituted Binaphthols

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In order to extend the scope of asymmetric conjugate alkenylation catalyzed by 3,3′-disubstituted binaphthols, two classes of compounds were examined. Asymmetric 1,4-addition of alkenylboronates onto N-acylimines was investigated. Chiral allylic amides were obtained in good yields and high enantios...

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Main Author: Chan, Sin Hang
Language:en
Published: 2009
Subjects:
asymmetric
conjugate addition
Chemistry
Online Access:http://hdl.handle.net/10012/4245
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spelling ndltd-LACETR-oai-collectionscanada.gc.ca-OWTU.10012-42452013-10-04T04:09:07ZChan, Sin Hang2009-01-23T19:59:55Z2009-01-23T19:59:55Z2009-01-23T19:59:55Z2009http://hdl.handle.net/10012/4245In order to extend the scope of asymmetric conjugate alkenylation catalyzed by 3,3′-disubstituted binaphthols, two classes of compounds were examined. Asymmetric 1,4-addition of alkenylboronates onto N-acylimines was investigated. Chiral allylic amides were obtained in good yields and high enantioselectivities. This represents one of the very few methods for synthesizing chiral allylic amides without the use of transition metal catalysts. Chiral binaphthol-catalyzed conjugate addition of alkenylboronates to -silyl--unsaturated ketones afforded highly enantioenriched chiral -silylcarbonyls. Asymmetric addition onto -silyl-enones is still a largely unexplored area, with only a handful of transition metal-catalyzed reactions reported. The first asymmetric reaction using these silicon-containing enones without using transition metal were described.enasymmetricconjugate additionAsymmetric Conjugate Addition of Boronates to N-Acylimines and β-Silyl-α,β-unsaturated Ketones Catalyzed by 3,3'-Disubstituted BinaphtholsThesis or DissertationChemistryMaster of ScienceChemistry
collection NDLTD
language en
sources NDLTD
topic asymmetric
conjugate addition
Chemistry
spellingShingle asymmetric
conjugate addition
Chemistry
Chan, Sin Hang
Asymmetric Conjugate Addition of Boronates to N-Acylimines and β-Silyl-α,β-unsaturated Ketones Catalyzed by 3,3'-Disubstituted Binaphthols
description In order to extend the scope of asymmetric conjugate alkenylation catalyzed by 3,3′-disubstituted binaphthols, two classes of compounds were examined. Asymmetric 1,4-addition of alkenylboronates onto N-acylimines was investigated. Chiral allylic amides were obtained in good yields and high enantioselectivities. This represents one of the very few methods for synthesizing chiral allylic amides without the use of transition metal catalysts. Chiral binaphthol-catalyzed conjugate addition of alkenylboronates to -silyl--unsaturated ketones afforded highly enantioenriched chiral -silylcarbonyls. Asymmetric addition onto -silyl-enones is still a largely unexplored area, with only a handful of transition metal-catalyzed reactions reported. The first asymmetric reaction using these silicon-containing enones without using transition metal were described.
author Chan, Sin Hang
author_facet Chan, Sin Hang
author_sort Chan, Sin Hang
title Asymmetric Conjugate Addition of Boronates to N-Acylimines and β-Silyl-α,β-unsaturated Ketones Catalyzed by 3,3'-Disubstituted Binaphthols
title_short Asymmetric Conjugate Addition of Boronates to N-Acylimines and β-Silyl-α,β-unsaturated Ketones Catalyzed by 3,3'-Disubstituted Binaphthols
title_full Asymmetric Conjugate Addition of Boronates to N-Acylimines and β-Silyl-α,β-unsaturated Ketones Catalyzed by 3,3'-Disubstituted Binaphthols
title_fullStr Asymmetric Conjugate Addition of Boronates to N-Acylimines and β-Silyl-α,β-unsaturated Ketones Catalyzed by 3,3'-Disubstituted Binaphthols
title_full_unstemmed Asymmetric Conjugate Addition of Boronates to N-Acylimines and β-Silyl-α,β-unsaturated Ketones Catalyzed by 3,3'-Disubstituted Binaphthols
title_sort asymmetric conjugate addition of boronates to n-acylimines and β-silyl-α,β-unsaturated ketones catalyzed by 3,3'-disubstituted binaphthols
publishDate 2009
url http://hdl.handle.net/10012/4245
work_keys_str_mv AT chansinhang asymmetricconjugateadditionofboronatestonacyliminesandbsilylabunsaturatedketonescatalyzedby33disubstitutedbinaphthols
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