121194-48-7Relevant academic research and scientific papers
A caveat on the sharpless asymmetric dihydroxylation
Iwashima, Makoto,Kinsho, Takeshi,Smith III, Amos B.
, p. 2199 - 2202 (1995)
Sharpless asymmetric dihydroxylation (AD) of the homochiral synthetic intermediates 2a-c gave anomalous results: pairs of pseudoenantiomeric reagents, expected to generate complementary diastereomer ratios characteristic of double diastereoselection, inst
A Practical Synthesis of (R)-Methoxy(phenyl)acetic Acid
Takano, Seiichi,Yanase, Masashi,Ogasawara, Kunio
, p. 39 - 40 (1989)
(R)-Methoxy(phenyl)acetic acid is efficiently prepared from (2S,3S)-3-phenylglycidol in two steps.
A concise enantioselective synthesis of (+)-goniodiol and (+)-8-methoxygoniodiol via Co-catalyzed HKR of anti-(2SR, 3RS)-3-methoxy-3- phenyl-1, 2-epoxypropane
Kiran, I.N. Chaithanya,Reddy, R. Santhosh,Suryavanshi, Gurunath,Sudalai, Arumugam
scheme or table, p. 438 - 440 (2011/03/18)
A short, enantioselective synthesis of (+)-goniodiol and (+)-8-methoxygoniodiol, cytotoxic styryllactones, has been achieved in high optical purities (99% ee). The strategy employs Co-catalyzed HKR of racemic anti-(2SR, 3RS)-3-methoxy-3-phenyl-1, 2-epoxypropane and Lewis acid-mediated diastereoselective allylation of aldehyde as chiral inducing key reactions.
Oxirane Ring-Opening with Alcohol Catalyzed by Organotin Phosphate Condensates. Complete Inversion at Tertiary and Benzylic Centers
Otera, Junzo,Niibo, Yoshihisa,Nozaki, Hitosi
, p. 7625 - 7634 (2007/10/02)
Regio- and stereospecific ring-opening of chiral oxiranes has been effected by organotin phosphate condensates catalyst.Alcohols attack on the tertiary and benzylic positions exclusively.Despite seemingly acidic character of the catalyst in terms of regioselectivity the chiral centers are completely inverted.The new methodology is applied to synthesis of enantiomerically pure linalool and to conversion of commercially available (R)-styrene oxide into the (S)-counterpart.
