Phosphine Oxide-Catalysed Chlorination Reactions of Alcohols Under Appel conditions
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1 osphine xide-catalysed Chlorination eactions of Alcohols Under Appel conditions Denton,. M.; An, J.; Adeniran, B. Chem. Commun. 2010, 46, H C C 2 catalytic Catalysis of osphorus(v)-diated Transformations: Dichloronation eactions of Epoxides Under Appel Conditions Denton,. M.; Tang, X.; rzeslak, A. rg. Lett. 2010, 12, C C 2 catalytic A Concise Synthesis of Honokiol Denton,. M.; Scragg, J. T.; Galofré, A. M.; Gui, X.; Lewis, W. Tetrahedron 2010, 66, H H
2 oss M. Denton : D with rofessor J.C. Anderson (University of Nottingham) : ostdoctoral studies with K.C. Nicolaou (Scripps esearch Institute) : ostdoctoral studies with Steven Ley (University of Cambridge) June 2009: Appointed to a permanent lectureship (University of Nottingham) esearch Interests New Chemistry and catalysis: Atom efficient and environmentally friendly construction of chemical bonds. New catalytic organophosphorus chemistry Natural roducts and Biological Study: Construction of plant derived natural products (>10 steps) for study of neurodegenerative diseases.
3 Appel eaction H CX 4, 3 X ' X=, ' chanism 3 C 3 ' H ' ' '
4 Development of a Catalytic Chlorination eaction C 9 H 19 5 H X mol % 3, 1 equiv (C) 2 CH 3 C 9 H 19 6 H C 9 H 19 7 C 9 H 19 8 C 9 H 19 Entry 3 (mol %) Addition protocol/addition time (% of 6) (% of 7) (% of 8) added to (C) added to (C) added to (C) added to (C)2 3 over 2 hrs and (C)2 added to (C)2 3 over 7hrs and (C)2 added to (C)2 over 7hrs and (C)2 added to (C)2 3 over 7hrs and (C)2 added to (C)2 3 over 5hrs
5 Substrate Scope H 15 mol % 3, 1 equiv (C) 2 CH 3 C 9 H 19 83% 80% 73% 70% C 9 H 19 C 6 H 15 48% 67% 88%
6 Substrate Scope Continued ' 15 mol % 3, ' H 1 equiv (C) 2 CH 3 69% 64% 7%
7 chanistic Studies Cycle 1 Cycle 2 C C 2 CC 3 H H 1 H NM Study C 9 H 19 H (C) 2 CD 3 1 eq. 3 C 9 H C, 16 hrs; reflux 2hrs C 9 H 19!!
8 Catalysis of osphorus(v)-diated Transformations: Dichloronation eactions of Epoxides Under Appel Conditions C C 2 catalytic Denton,. M.; Tang, X.; rzeslak, A. rg. Lett. 2010, 12,
9 revious Dichloronation of Epoxides n(h 2 C) n =1, 2, 6 3, C 4 reflux 2-5 days n(h 2 C) 70-80% yield Croft, A..; Bartsch,. A. J. rg. Chem. 1983, 48, Bn 3 /NCS TBDS toluene, 90 C Bn TBDS 42% yield Yoshimitsu, T.; Fukumoto, N.; Tanaka, T. J. rg. Chem. 2009, 74, shorter reaction times
10 eaction ptimization 9 3, (C) 2 2,6-tBuy CH 3 9 Entry 3 (mol %) (C)2 (mol %) 2,6-tBuy (mol %) time (h) yield (%)
11 Substrate Scope 1 15 mol % 3, equiv (C) equiv 2,6-tBuy 6h % 78% 57% 66% TBDS C 2 Et 62% 57% 66%
12 chanistic Studies C C 2 CC 2 1
13 A Concise Synthesis of Honokiol H H honokiol H H chavicol H magnolol Family or biaryl neolignans isolated from Magnoliae officinalis in 1972 Extracts from this bark used for traditional Chinese and Japanese medicine Honokiol used a muscle relaxant as early as 1975 btained by extraction from magnolia bark Anticancer activity and neurotrophic activity 1986 first total synthesis (4 steps, 16% yield) 2004 second total synthesis (14 steps, 21% yield)
14 Initial etrosynthetic Approach H sigmatropic rearrangements honokiol H retro Friedel Crafts alkylation alkylation demethylation H direct arylation H
15 Forward Synthesis, First Approach H [h(cd)] 2 (10 mol%) (N 2 ) 3 (30 mol%), Cs 2 C 3, toluene, reflux, 18 hrs 45% yield H 1) B 3 S 2, DCE, reflux, 18 hrs, 66% yield 2) Allyl bromide, Cs 2 C 3 DMF, 23 C, 15 hrs 92% yield H H DMF, MW, 200 C, 1hr 49%
16 etro Friedel-Crafts Alkylation H Al 3, toluene:n 2 (10:1) H H 60 C, 2 hrs 63% yield H H Al 3, toluene:n 2 (10:1) H H 60 C, 2 hrs decomposition H H Al 3, toluene:n 2 (10:1) H H 23 C, 2 hrs no reaction H
17 evised etrosynthetic Approach H aisen rearrangement honokiol H deprotection Suzuki coupling allylation H lithiation (H) 2 B
18 Forward Synthesis, Second Approach (H) 2 B H d(dba) 3 (10 mol%) S-os (30 mol%) KF (5 equiv.) THF/H 2, 15 hrs 94% yield H S-os Cy 2 H allyl bromide, K 2 C 3 acetone, reflux, 18 hr 99% yield honokiol H B 3 S 2, DCE, reflux, 18 hrs, 47% yield H H
19 Forward Synthesis, Second Approach (H) 2 B H d(dba) 3 (10 mol%) S-os (30 mol%) KF (5 equiv.) THF/H 2, 15 hrs 94% yield H S-os Cy 2 allyl bromide, K 2 C 3 acetone, reflux, 18 hr 99% yield H 1) 1,2-dichlorobenzene 200 C, MW, 15 min 86% yield honokiol H 2) B 3 S 2, DCE, reflux, 18 hrs, 91% yield
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