A Route to Carbasugar Analogues - Jonathan Clayden - The ...

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Chapter 2 – Dearomatising additions to aryl oxazolines Further suggestions for future work have been made throughout this discussion and a number have already been undertaken. Future improvements in the methodology will require further close study of the reaction conditions, which may prove to be substrate dependent. A number of ways to improve reactions involving organolithiums have recently be suggested by Collum. 67 93
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Dearomatising Addition of Organolit
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2.3 Synthetic Scope 64 2.3.1 Organo
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Abstract Dearomatising Addition of
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The Author The Author graduated fro
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Abbreviations & Conventions Ac acet
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RDS rate determining step R f RC rt
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Chapter 1: Introduction Chapter 1 -
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Chapter 1: Introduction controlled
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Chapter 1: Introduction diastereome
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Chapter 1: Introduction combine mor
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Chapter 1: Introduction O Ar Cl TMP
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Chapter 1: Introduction conditions,
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Chapter 1: Introduction chiral oxaz
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Chapter 1: Introduction Again a lar
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Chapter 1: Introduction 34 Scheme 1
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Chapter 1: Introduction The amino a
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Chapter 1: Introduction It was envi
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Chapter 1: Introduction COR' i) ATP
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Chapter 1: Introduction O i) ATPH,
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Chapter 1: Introduction 1.4 Nucleop
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Page 44 and 45: Chapter 1: Introduction Diene (-)-8
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Page 50 and 51: Chapter 2 - Dearomatising additions
Page 94 and 95: Chapter 3 - Oxazoline synthesis & r
Page 130 and 131: Chapter 4 - Synthesis of carbasugar
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Chapter 4 - Synthesis of carbasugar
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References References for Chapters
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References (73) Betson, M. S.; Clay
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References (139) Yoon, Y.-J.; Joo,
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References (202) Meyers, A. I.; Tem
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Experimental section Chapter 5 - Ex
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Experimental section was triturated
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Experimental for chapter 2 5.2 Expe
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Experimental for chapter 2 Synthesi
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Experimental for chapter 2 Synthesi
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Experimental for chapter 2 103c R f
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Experimental for chapter 2 102j R f
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Experimental for chapter 2 105 R f
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Experimental for chapter 2 5.55 (dd
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Experimental for chapter 3.1 5.3 Ex
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Experimental for chapter 3.1 ν max
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Experimental for chapter 3.1 CHOH),
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Experimental for chapter 3.1 over c
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Experimental for chapter 3.1 R f :
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Experimental for chapter 3.1 Synthe
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Experimental for chapter 3.1 101b d
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Experimental for chapter 3.1 (d, 1H
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Experimental for chapter 3.1 101j R
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Experimental for chapter 3.2 324.19
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Experimental for chapter 3.2 5.56 (
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Experimental for chapter 3.2 10.0,
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Experimental for chapter 4.1 Ph), 7
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Experimental for chapter 4.1 2.30 (
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Experimental for chapter 4.1 ¹³C-
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Experimental for chapter 4.2 (d, 3H
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Experimental for chapter 4.2 Data f
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Appendix A: Selected NMR Spectra 27
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Appendix B - Crystallographic Infor
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_audit_creation_method SHELXL-97 _c
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_refine_ls_shift/su_mean 0.000 loop
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C7 0.0311(13) 0.0244(13) 0.0347(13)
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O1 C4 C5 111.68(17) . . ? C6 C5 C4
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C21 C22 C23 C24 0.4(3) . . . . ? C2
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The structure was solved by the dir
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_refine_ls_extinction_coef ? _refin
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_atom_site_aniso_U_12 O1 0.0253(7)
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C21 C3 H3 109.7 . . ? C2 C3 H3 109.
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C17 C18 C19 C20 -0.8(3) . . . . ? C
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Final R indices [I>2sigma(I)] R1 =
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_diffrn_reflns_limit_k_min -11 _dif
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H8 H 0.9757 -0.1848 0.2244 0.024 Ui
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C43 C 0.4196(12) 0.2863(7) 0.6783(6
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C42 0.072(7) 0.028(5) 0.057(6) 0.01
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C29 C35 1.548(8) . ? C29 C30 1.554(
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C20 C21 H21 119.7 . . ? C21 C22 C23
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C1 C4 C5 C11 64.4(7) . . . . ? C11
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d. Compound 278 HO OH HO OH 278 OH
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_exptl_crystal_description plate _e
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_refine_ls_restrained_S_all 1.154 _
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C18 C 0.4218(4) 0.5303(6) 0.6578(3)
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loop_ _geom_bond_atom_site_label_1
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C2 C9 H9 106.9 . . ? C9 C10 H10A 10
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O9 C16 C17 C12 -179.9(4) . . . . ?
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