STEREOSELECTIVE HYDRIDE REDUCTIONS OF CHIRAL 2-P-TOLYLSULFINYLCYCLOALKANONES

Authors
BUENO AB CARRENO M RUANO JLG PENA B RUBIO A HOYOS MA
Citation
Ab. Bueno et al., STEREOSELECTIVE HYDRIDE REDUCTIONS OF CHIRAL 2-P-TOLYLSULFINYLCYCLOALKANONES, Tetrahedron, 50(31), 1994, pp. 9355-9364
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
31
Year of publication
1994
Pages
9355 - 9364
Database
ISI
SICI code
0040-4020(1994)50:31<9355:SHROC2>2.0.ZU;2-L
Abstract
The highly stereoselective hydride reductions of chiral 2-p-tolylsulfi nyl-cyclopentanones and cycloheptanones are described. With DIBAL (ele ctrophilic hydride) the configuration induced at C-1 is controlled by the sulfinyl group (1,3-asymmetric induction), and it can be inverted by using ZnCl2 as catalyst. With L-selectride the stereoselectivity is directed by the C-2 chiral groups (1,2-asymmetric induction). Other n ucleophilic hydrides gave results which depend on the reagents and the size of the rings.