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Enantioselective artificial equipment are usually not merely within the vanguard of chemical and pharmaceutical learn yet job during this quarter is consistently expanding. it truly is inspired through the urgency to procure medicinal drugs or compounds of medicinal curiosity as unmarried anantiomers, and the keeness to synthesize usual items in nonracemic shape. This quantity offers seven chapters from pioneers and experts during this quickly increasing box.

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Extra resources for Advances in Asymmetric Synthesis, Volume 1, Volume 1 (Advances in Asymmetric Synthesis)

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1 NBng syn NBn 2 antf 73 27 TiCI4 62 38 (25%) EtAICI2 >99 <1 (71%) SnCI4 Al (59%) ,AI Bn 2 NO F • ^ H H C D chelation (more reactive) non-chelation (less reactive) X OSiMe 3 <^OR (less reactive) (more reactive) \1 \f syn Scheme 23. 17 18 KOICHI MIKAMI A H • MLn -78 °C WWFW NHBoc OH 1 „ NHBoc syn y^XA 1 NHBoc anti SnCI4 >99 <1 (41%) EtAICI2 34 66 (40%) Scheme 24. principle30 and the order of the nucleophile reactivity: alkenes (ene) < allylic silanes < enol silanes. EtAlCb should be favorable for monodentate complexation.

E. Asymmetric Catalysis Asymmetric catalysis of carbonyl-ene reactions was initially investigated in the more facile intramolecular versions. 91 It is still, however, a stoichiometric asymmetric transfer even in the presence of MS 4A. 1 eg) ^—' MS4A o toluene R=H R = Me 20 days 4days 17% 39% (82% ee) mesitylene 32% (86% ee) CFCI2CF2CI 63% (>98%ee) Scheme 51. ,4S)-cfe (3R,4R)-trans 80 (84% ee) (fl)-4: X = CIO4 20 (74% ee) 47 53 (70% ee) (79% ee) (fl)-1:X = d Scheme 52. OH (fl)-4 J-H (20mol%) MS4A "I R'T^ FUH 91% ee (A) R = Me 82% ee (A) Scheme 53.

The formation of larger rings by (3,4) ene cyclizations is rare {vide infra). ) carbonylene cyclizations, respectively. 74'75 Such an ene cyclization has recently been recognized as an efficient method for stereocontrolled cyclization with C-C bond formation ("carbo-cyclization"). A. )-glyceraldehyde acetonide via 34 KOICHI MIKAMI \r COgEt 180 °C N^'CH 2 OSi^ C

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