01621nas a2200181   4500008004100000022001400041245018100055210006900236260011000305300001600415490000600431520079500437100002401232700002501256700001501281700001701296856012601313       2016                        eng d  a2046-206900aExploration of the diastereoselectivity in an unusual Grignard reaction and its application towards the synthesis of styryl lactones 7-epi-(+)-goniodiol and 8-epi-(-)-goniodiol0 aExploration of the diastereoselectivity in an unusual Grignard r  aTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLANDbROYAL SOC CHEMISTRYcMAY  a50721-507250 v63 a<p>An unusual diastereoselective Grignard reaction is explored, where the Grignard reagents are derived from 1,n-dihaloalkanes. A steric bias due to the presence of a quaternary centre adjacent to the acetonide ester at the benzylic position is responsible for the formation of an intramolecularly reduced product in almost quantitative yield. This steric hindrance is responsible for the diastereoselectivity observed with a variety of aromatic as well as aliphatic esters. The unusual Grignard reaction furnishes long chain secondary alcohols possessing a terminal olefin, which are synthetically important intermediates. As an application of this method, the diastereoselective synthesis of styryl lactones viz. 7-epi-(+)-goniodiol (29) and 8-epi(-)-goniodiol (30) has been achieved.</p>1 aChavan, Subhash, P.1 aKhatod, Harshali, S.1 aDas, Tamal1 aVanka, Kumar  uhttps://library.ncl.res.in/content/exploration-diastereoselectivity-unusual-grignard-reaction-and-its-application-towards