New PDF release: Active Metals

By Furstner A

ISBN-10: 3527273557

ISBN-13: 9783527273553

ISBN-10: 3527279385

ISBN-13: 9783527279388

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Table 1-7 shows representative spiro-ylactones that have been prepared in this way. We have recently reported an extension of this methodology in the production of spiro-d-lactones [37]. Much work has been done to elucidate novel synthetic routes for these types of molecules [38]. In particular, d-substituted d-lactones have recently attracted considerable attention, mainly because molecules of this class include many natural products that exhibit significant biological activity [39]. Scheme 1-9 illustrates a route for the synthesis of spiro d-lactones from the magnesium complex of 1,2-bis(methylene)cyclohexane 1 [40].

Table 1-5. Rcactions of diene-magnesium reagents with carboxylic esters. Formation of cyclopentenols. ~~ Entry l 3 o Diene = Ester Product Yielda) CH3COOEt 91 CH3(CH2)2COOEt 96 PhCOOEt 55 = a< CH3(CH2)2COOEt a) Fused bicyclic product was obtained under reflux. 59 74 16 I Rieke Metals: Highly Reactive Metal Powders Table 1-6. Reactions of diene-magnesium reagents with carboxylic esters. Formation of ketones. Entry Diene Ester Product /3. y-unsaturated Yielda' (YO) CH&X)OEt 72 CH3(CH&COOEt ni PhCOOEt 62 CH3(CH2)2COOEt 76 84 a) Quenching the reaction at - 10 "C gave the /3.

Reaction of thc 1,2-bis(methylene)cyclohcxane-magnesiurn complex with an ester. Table 1-4. Reactions of magnesium complexes of 1,2-dimethylenecycloalkaneswith bis-electrophiles. Entry Dimea) Electrophile Yieldb) (96) Product Reaction conditionc) A la la Br(CH2)4Br la Br(CH2)dBr la la a 75(81) 81 (CH,),Br 75(87) 14 I Riekr Metals: Highly Rructive Metal Powders Table 1-4. (continued) Entry Dieilea) Electrophilc Product Yieldb)(a) Reaction condition'" 7 la -(78) F 8 la 415) B 9 la 440) B 10 la 52(67) €3 11 Ib 60(70) D 12 lc 73 C 13 Ic 77(86) D 14 Ic 46(59) R 15 la 89 B a) (1 a) 1,2-bis(methylene)cyclohexane; (1 b) 1,2-bis(methylene)cycIopentane; ( I c) I ,2-bis(methylene)cycloheptane.

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Active Metals by Furstner A

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