Helvetica Chimica Acta p. 1477 - 1488 (1991)
Update date:2022-07-30
Topics:
Bienz, Stefan
Chapeaurouge, Alexander
The synthesis of the three alkoxymethyl-sustituted acylsilanes 1-3 is described (Schemes 1 and 2).Their reactions with NaBH4 as well as PhLi gave the corresponding alcohols with moderate to good diastereoisomeric induction (up to 78percent de; see Table), depending upon the solvent used (Scheme 3).The results indicate that in Et2O, the reactions with PhLi proceed via 6-membered chelates (see C in Scheme 4) leading to the products with high de's (74 - 78percent).In THF, these chelates are not formed, and as a consequence, the additions take place with reversed and lower stereoselectivities (34 - 50percent de).
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