Active Metals by Furstner A

By Furstner A

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Lic enol 2,3,4,5,6,7-hexahydro-2-methyllti-inden-2-01 (4) was obtained. It was found that the initial product generated upon treating the 1,2-bis(methylene)cycloalkanemagnesium, 1, with ethyl acetate was 2, a magnesium salt of a spiroenol containing a cyclopropane ring. This intermediate underwent ring expansion upon warming, to produce the fused carbocyclic product 4. Alternatively, protonation of the intermediate 2 at -10 "C generated the corresponding spiroenol 5, which underwent an in-situ rearrangement to afford the P,y-unsaturated ketone 6 .

A one-to-one mixture of aldehyde or ketone and a-bromoester is then added at -5 "C. After stirring for one hour at room temperature the reaction is followed by thc normal work-up procedure r541. Scheme 1-12. Reformatsky reaction. The formation of organozincs from alkyl, aryl, and vinyl bromides or chlorides was formerly possible only by a metathesis reaction of a zinc halide salt with a preformed organolithium or Grignard reagent. 3 Hieke Zinc Table 1-12. 2: 1 1:l 2: 1 2: 1 23 23 23 23 reflux reflux reflux reflux reflux reflux 4 6 3: I 2: I 2: I 3: 1 3: 1 25 3 3 3 3 2 2 4 4 Yield (%) 100 100 100 100 90 I00 100 100 100 100 agents are not compatible with many types of functionality, which limit their utility.

Also, the manner in which the CuCN . nLiX and lithium naphthalenide are added together affects thc reactivity of the resulting active copper solution. The best results were obtained when the CuCN . nLiX was added into the preformed lithium naphthalenide. It should be noted that the phosphine-based active copper is more reactive than the active copper derived from CuCN . nLiX. rzLiX offers several advantages. First, CuCN is an inexpensive and stable source of Cu' which can be used as received without further purification.

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