Verfügbarkeit: IDPi catalysis

IDPi catalysis: the Hosomi-Sakurai allylation and a Mukaiyama aldol reaction with enolsilanes of acetaldehyde

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Bibliographische Detailangaben
1. Verfasser:	Schreyer, Lucas (VerfasserIn)
Format:	Abschlussarbeit Buch
Sprache:	English
Veröffentlicht:	Köln 2018
Schlagworte:	Katalyse Asymmetrische Synthese Allylierung Hochschulschrift
Online-Zugang:	Inhaltsverzeichnis Inhaltsverzeichnis
Beschreibung:	IX, 235 Seiten Illustrationen 21 cm

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adam_text	CONTENTS ACKNOWLEDGEMENTS......................................................................................................................... I ABSTRACT..........................................................................................................................................IV KURZZUSAMMENFASSUNG...................................................................................................................V ABBREVIATIONS................................................................................................................................ VI 1 INTRODUCTION............................................................................................................................ 1 2 ENANTIOSELECTIVE HOSOMI-SAKURAI ALLYLATION OF ALDEHYDES .............................................. 10 2.1 LITERATURE BACKGROUND.................................................................................................. 10 2.1.1 STEREOCHEMICAL MODELS......................................................................................... 10 2.1.2 CHIRAL ALLYLATING AGENTS......................................................................................... 11 2.1.3 CATALYTIC ENANTIOSELECTIVE ALLYLATIONS OF ALDEHYDES.............................................13 2.1.4 ALLYLATIONS WITH ALLYLTRIMETHYLSILANE: THE HOSOMI-SAKURAI REACTION..................15 2.2 OBJECTIVE........................................................................................................................ 18 2.3 RESULTS AND DISCUSSION.................................................................................................. 19 2.3.1 AROMATIC ALDEHYDES - CATALYST OPTIMIZATION.......................................................21 2.3.2 AROMATIC ALDEHYDES - SUBSTRATE SCOPE AND LIMITATIONS .................................... 23 2.3.3 ALIPHATIC ALDEHYDES - CATALYST OPTIMIZATION.......................................................24 2.3.4 ALIPHATIC ALDEHYDES - SUBSTRATE SCOPE AND LIMITATIONS ..................................... 29 2.4 SUMMARY AND OUTLOOK.................................................................................................. 33 3 ENANTIOSELECTIVE MUKAIYAMA ALDOL REACTION WITH ENOLSILANES OF ACETALDEHYDE ............ 34 3.1 LITERATURE BACKGROUND.................................................................................................. 34 3.2 OBJECTIVE........................................................................................................................ 42 3.3 RESULTS AND DISCUSSION .... . .............................................................................................43 3.3.1 AROMATIC ALDEHYDES - CATALYST OPTIMIZATION, SUBSTRATE SCOPE AND LIMITATIONS ................................................................................................................................ 45 3.3.2 ALIPHATIC ALDEHYDES - CATALYST OPTIMIZATION.......................................................48 3.3.3 ALIPHATIC ALDEHYDES - SUBSTRATE SCOPE AND LIMITATIONS ..................................... 60 3.3.4 MECHANISTIC INVESTIGATIONS....................................................................................64 3.4 SUMMARY AND OUTLOOK.................................................................................................. 68 4 EXPERIMENTAL SECTION...........................................................................................................70 4.1 GENERAL WORKING METHODS........................................................................................... 70 4.2 SYNTHETIC PROCEDURES: HOSOMI-SAKURAI ALLYLATION OF ALDEHYDES ............................... 74 4.2.1 SCOPE OF AROMATIC ALDEHYDES AND ENALS .............................................................. 74 4.2.2 ALIPHATIC SUBSTRATE SCOPE......................................................................................82 4.3 MUKAIYAMA CROSS-ALDOL REACTION: SYNTHETIC PROCEDURES .......................................... 88 4.3.1 AROMATIC SUBSTRATE SCOPE.....................................................................................89 4.3.2 ALIPHATIC SUBSTRATE SCOPE.................................................................................... 101 4.3.2 ALDOL REACTIONS WITH PROPANAL-DERIVED ENOLSILANES (E)- AND (Z)-121B.............110 4.3.3 SYNTHESIS OF RACEMATES....................................................................................... 112 4.3.4 FORMAL SYNTHESIS OF (S)-DULOXETINE FROM ALDOL 118V ......................................... 113 4.3.5 SYNTHESIS OF ENOLSILANES 111 AND 121B .............................................................. 114 4.4 MUKAIYAMA CROSS-ALDOL REACTION: MECHANISTIC STUDIES...........................................119 4.4.1 REACTION PROGRESS KINETIC ANALYSIS ..................................................................... 119 4.4.2 THE EFFECT OF THE SILYL GROUPS..............................................................................158 4.4.3 STOICHIOMETRIC EXPERIMENTS................................................................................161 4.4.4 LOW TEMPERATURE NMR EXPERIMENTS ................................................................. 162 4.5 SYNTHESES OF CATALYSTS AND THEIR PRECURSORS ............................................................. 171 REFERENCES.................................................................................................................................. 222 APPENDIX..................................................................................................................................... 234 ERKLAERUNG ZUR DISSERTATION..................................................................................................... 234 TEILPUBLIKATIONEN....................................................................................................................235
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spelling	Schreyer, Lucas Verfasser (DE-588)1168484707 aut IDPi catalysis the Hosomi-Sakurai allylation and a Mukaiyama aldol reaction with enolsilanes of acetaldehyde vorgelegt von Lucas Schreyer aus Wien Köln 2018 IX, 235 Seiten Illustrationen 21 cm txt rdacontent n rdamedia nc rdacarrier Dissertation Universität zu Köln 2018 Katalyse (DE-588)4029921-1 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Allylierung (DE-588)4336304-0 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Katalyse (DE-588)4029921-1 s Allylierung (DE-588)4336304-0 s Asymmetrische Synthese (DE-588)4135603-2 s DE-604 B:DE-101 application/pdf http://d-nb.info/1172924066/04 Inhaltsverzeichnis DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030932234&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis
spellingShingle	Schreyer, Lucas IDPi catalysis the Hosomi-Sakurai allylation and a Mukaiyama aldol reaction with enolsilanes of acetaldehyde Katalyse (DE-588)4029921-1 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Allylierung (DE-588)4336304-0 gnd
subject_GND	(DE-588)4029921-1 (DE-588)4135603-2 (DE-588)4336304-0 (DE-588)4113937-9
title	IDPi catalysis the Hosomi-Sakurai allylation and a Mukaiyama aldol reaction with enolsilanes of acetaldehyde
title_auth	IDPi catalysis the Hosomi-Sakurai allylation and a Mukaiyama aldol reaction with enolsilanes of acetaldehyde
title_exact_search	IDPi catalysis the Hosomi-Sakurai allylation and a Mukaiyama aldol reaction with enolsilanes of acetaldehyde
title_full	IDPi catalysis the Hosomi-Sakurai allylation and a Mukaiyama aldol reaction with enolsilanes of acetaldehyde vorgelegt von Lucas Schreyer aus Wien
title_fullStr	IDPi catalysis the Hosomi-Sakurai allylation and a Mukaiyama aldol reaction with enolsilanes of acetaldehyde vorgelegt von Lucas Schreyer aus Wien
title_full_unstemmed	IDPi catalysis the Hosomi-Sakurai allylation and a Mukaiyama aldol reaction with enolsilanes of acetaldehyde vorgelegt von Lucas Schreyer aus Wien
title_short	IDPi catalysis
title_sort	idpi catalysis the hosomi sakurai allylation and a mukaiyama aldol reaction with enolsilanes of acetaldehyde
title_sub	the Hosomi-Sakurai allylation and a Mukaiyama aldol reaction with enolsilanes of acetaldehyde
topic	Katalyse (DE-588)4029921-1 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Allylierung (DE-588)4336304-0 gnd
topic_facet	Katalyse Asymmetrische Synthese Allylierung Hochschulschrift
url	http://d-nb.info/1172924066/04 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030932234&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
work_keys_str_mv	AT schreyerlucas idpicatalysisthehosomisakuraiallylationandamukaiyamaaldolreactionwithenolsilanesofacetaldehyde

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