Page 1341 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1318 Reformatsky reaction, 657–660 SEM, see 2-(trimethylsilyl) ethoxymethyl
Resolution, in enantioselective synthesis, 1166, Semibenzilic rearrangement, 894
Index 1172–1173, 1183 Shapiro reaction, 454–456, 631
Retrosynthetic analysis, 1163, 1164–1166 Sharpless epoxidation, 1085–1088
antisynthetic transforms, 1164 [2,3]-sigmatropic rearrangments, 581–590
convergent steps, 1163 N-allyl amine oxides, 582
bond disconnections, 1164, 1174 allyl ether anions, 587–588
Rhodium compounds, catalysis by examples, 587, 589
carbenoid cyclopropanation, 919, 920, 921, in juvabione synthesis, 1182–1185
923–929 stereochemistry of, 587–588
computational model for, 925, 927–929 allyl sulfoxides, 581–582
insertion reactions, 934–940 allyl selenoxides, 582
intramolecular, 938, 939 ammonium ylides, 583–586
hydroformylation, 759–760 examples, 587
Robinson annulation reaction, 134–139, 143 sulfonium ylides, 581–586
enantioselective catalysis by praline, 133, examples, 586
142, 512 [3,3]-sigmatropic rearrangements, 552–581
examples, 137, 138 anionic oxy-cope, 556–557
Ruthenium catalysts N−allyl amide enolates, 577, 578
olefin metathesis, 761–766 N-allyl amine oxides, 588
Ruthenium tetroxide
O-allyl ketene aminals, 576–579
as oxidant, 1067, 1069, 1070
Claisen, 560–564
Cope, 552–560
examples, 552
Sakurai reaction, 815–827
imidates, 577–578
catalysts for, 815, 816
Ireland-Claisen rearrangement, 567–576
enatioselective, 821, 823, 825, 827
ketene aminals, 576–577
mechanism of 813, 816–817, 824
orthoester Claisen rearrangement, 564–567
stereoselectivity of, 817–822
Silanes
Samarium salts
reductive coupling, 446–447 allylic, 784
reductive elimination, 174–175 acylation, 829–830
SAMP, see addition to carbonyl compounds, 815–828;
(S -N-amino2-methoxymethylpyrrolidine see also sakurai reaction
Sandmeyer reaction, 1030 conjugate addition reactions, 830–833
Scandium triflate as catalyst fluoride induced reactions, 824
carbonyl ene reaction, 869–879 iminium ions, addition to, 825–829
Friedel-Crafts alkylation, 1014–1016, 1018, 1019 in discodermolide synthesis, 1235, 1237,
Schiemann reaction, 1031, 1032 1239, 1240
Schlosser modification of Wittig reaction, 162 alkenyl
Selectrides, see borohydrides, alkyl reactions
Selenenyl halides, 308–310, 333 acylation, 826
Selenides polyene cyclization, 864–868
radicals from, 958 synthesis from
Selenoxides aldehydes by organometallic addition, 813
allylic, [2,3]-sigmatropic rearrangement of, alkynes by carbometallation, 812–813
581–589 alkynes by hydrosilation, 810–813
thermal elimination reactions, 590, 591, 593, alkynes using boranes, 797
595, 601 as hydride donors, 425–429
Selenium dioxide oxidation of halo, reactions with aldehydes, 821–825
alkenes, 1124–1127 reactions with
ketones, 1143, 1144 carbonyl compounds, 815–820
Selenylation synthesis from, 809–813
alkenes, 307, 308, 309, 310 alkenes by hydrosilation, 809, 810
allylic oxidation by, 1124–1126 silyl halides and organometallic reagents,
reagents for, 308 808–810, 812
carbonyl compounds, 331–333 Siloxy-Cope rearrangement, 556–557
Selenylcyclization, 320–322 Silyl enol ethers
examples, 321, 322–324 alkylation, 863, 864