16507-88-3Relevant academic research and scientific papers
1,2-diastereoselection induced by chiral silicon in the addition of Grignard reagents to acylsilanes
Bonini, Bianca F.,Masiero, Stefano,Mazzanti, Germana,Zani, Paolo
, p. 6801 - 6804 (2007/10/02)
The reaction of acylsilanes 1 with Grignard reagents gives the diastereomeric α-hydroxysilanes 3. The level of asymmetric induction depends on the nature of R1 and R2. Good results were obtained for R1=t-Bu, R2=
Chiral Acylsilanes in Organic Synthesis. Diastereoselective 1,2 Additions to Racemic Alkoxymethyl-Substituted Acylsilanes
Bienz, Stefan,Chapeaurouge, Alexander
, p. 1477 - 1488 (2007/10/02)
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).
