By Trost B.M., Fleming I., Pattenden G. (eds.)

ISBN-10: 0080405940

ISBN-13: 9780080405940

Quantity three covers carbon-to-carbon unmarried bond forming reactions regarding sp 3, sp 2 and sp carbon facilities, yet in basic terms these which don't contain additions to C-X &pgr;-bonds. the amount first compares and contrasts the alkylation reactions of every kind of sp 3 carbon nucleophiles and likewise covers vinyl and alkynyl carbanions. Following on from quantity 2, a separate part covers Friedel-Crafts alkylation reactions, that's complemented through discussions of polyene cyclizations and electrophilic transannular cyclizations in synthesis. Coupling reactions resulting in &agr;-bond formation, and concerning every kind of combos of sp 3, sp 2 and sp carbon facilities are subsequent lined, together with these reactions in accordance with pinacol, acyloin and phenol oxidative coupling reactions, and likewise the Kolbe response. Rearrangement reactions, resulting in carbon-to-carbon &agr;-bond formation, are frequently utilized in a smart demeanour in synthesis. the amount contains all these rearrangement reactions in line with intermediate carbonium ions and carbanions, and likewise contains the benzil-benzilic acid and the Wolff rearrangements. the amount closes with insurance of carbonylation reactions, and using carbene insertion reactions into the C-H bond in synthesis.

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Additional info for Comprehensive Organic Synthesis: Carbon-Carbon sigma-Bond Formation

Sample text

7 Retrosynthetic Analysis of Squalene (57) Squalene (57) (Chart 8) is important as the biogenetic precursor of steroids and triterpenoids. Its structure contains as complicating elements six trisubstituted olefinic linkages, four of which are Estereocenters. Retrosynthetic analysis of 57 can be carried out under T-goal guidance by selecting transforms which are both C-C disconnective and stereocontrolled. The appropriate disconnective Tgoals must contain in the retron the E-trisubstituted olefinic linkage.

The synthetic conversion of 70 to 69 is clearly a favored pathway, which makes 70 a valid intermediate. The Sharpless oxidation transform converts 70 to 71. Intermediate 71 can be converted retrosynthetically in a few steps via 72 to 73, which contains the Sharpless oxidation retron, and a 2-carbon, nucleophile such as 74 (protection/deprotection required). Application of the AE (KR) transform to 73 produces the readily available (±) alcohol 75. Alternatively the chiral from of 75 might be obtained by enantioselective reduction of 76 and then converted by an AE process to the required 73.

G. O, N, S, P) which are easily generated synthetically are strategic for disconnection. Specific bonds in this category are ester, amide, imine, thioether, and acetal. 4. g. C6H5CH2CH2CH2CH2 rather than simply C6H5 (this is essentially a special case of rule 1, above). 5. e. rings within chains) into molecular segments is frequently best accomplished by acyclic bond disconnection, especially when such rings are separated by one or more chain members. e. exo) to a ring, or 1, 2, or 3 bonds removed from it, depending on the type of ring which is involved.

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Comprehensive Organic Synthesis: Carbon-Carbon sigma-Bond Formation by Trost B.M., Fleming I., Pattenden G. (eds.)


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