By Carey F.A., Sundberg R.J.

The two-part, 5th variation of complicated natural Chemistry has been considerably revised and reorganized for larger readability. the fabric has been up to date to mirror advances within the box because the past version, in particular in computational chemistry. half B describes the main basic and precious man made reactions, geared up at the foundation of response variety. it could stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes offer a entire origin for the learn in natural chemistry. better half web content supply electronic versions for college kids and workout strategies for teachers.

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In unfunctionalized enolates, alkylation usually takes place anti to the larger substituent, but with very modest stereoselectivity. 58 59 H. O. House, W. V. Phillips, and D. Van Derveer, J. Org. , 44, 2400 (1979). K. Ando, N. S. Green, Y. Li, and K. N. Houk, J. Am. Chem. , 121, 5334 (1999). 1° 37. 0 kcal/mol Fig. 4. Transition structures for syn and anti attack on the kinetic enolate of trans-2,3dimethylcyclopentanone showing the staggered versus eclipsed nature of the newly forming bond. Reproduced from J.

F. Elsinger, Org. , V, 76 (1973). 1) H2O, –OH 2) H+ CH2CH2CN Cl 24 CHAPTER 1 Alkylation of Enolates and Other Carbon Nucleophiles as the synthetic equivalent of acetone. Entries 2 and 3 show synthesis of carboxylic acids via the malonate ester route. Entry 4 is an example of a nitrile synthesis, starting with ethyl cyanoacetate as the carbon nucleophile. The cyano group also facilitates decarboxylation. Entry 5 illustrates an alternative decarboxylation procedure in which lithium iodide is used to cleave the -ketoester by nucleophilic demethylation.

1023 (2001). P. Duhamel, D. Cahard, Y. -M. Poirier, J. Org. , 61, 2232 (1996); Y. Quesnel, L. -M. Poirier, and L. Duhamel, Synlett, 413 (1998). For reviews of the chemistry of O-silyl enol ethers, see J. K. Rasmussen, Synthesis, 91 (1977); P. Brownbridge, Synthesis, 1, 85 (1983); I. Kuwajima and E. Nakamura, Acc. Chem. , 18, 181 (l985). 2. Other Means of Generating Specific Enolates A. 1 O–Li+ OSiMe3 CH(CH3)2 CH3 CH(CH3)2 CH3Li + (CH3)4Si DME CH3 CH3 CH3 b 2 + OSi(CH3)3 CH3 O– PhCH2N(CH3)3 + CH3 PhCH2N(CH3)3F– + (CH3)3SiF THF B.

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