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METAL DEPENDENT 1,3-ASYMMETRIC INDUCTION IN THE RETRO-[1,4]-BROOK REARRANGEMENT OF A SILYLATED TIGLYL ALKALIMETAL COMPOUND

✍ Scribed by Christoph Gibson; Thomas Buck; Mathias Noltemeyer; Reinhard Brückner*

Book ID
104256881
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
556 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

At -78°C in THF, the tiglyl phenyl sulfide 5 and lithium naphthdenidegave a tiglyl lithium specieswhichunderwentan irreversibleretro-[l,4]-Brookrearrangement givingrise to a 22:78 mixtureof the anti,trans and the syrr,transdinstereomerof the tiglyl silane 6. The same sulfide 5 and potassium naphthalenideprovidedthe same productsanti,tram-and syn,trans-6 as a 96:4 mixture.This time they arosefrom the reversibleretro-[1,4]-Brookrearrangement of a tiglylpotassiumintemrediate.

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