ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of the three alkoxymethyl-substituted acyisilanes 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 78% 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 (74-78%). In THF, these chelates are not formed, and as a consequence, the additions take place with reversed and lower stereoselectivities (34-50% de).
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19910740712
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