TY - JOUR
T1 - Stereo and reg ioselective openings of chiral 2,3-epoxy alcohols. versatile routes to optically pure natural products and drugs. unusual kinetic resolutions
AU - Sharpless, K. Barry
AU - Behrens, Carl H.
AU - Katsuki, Tsutomu
AU - LEE, Albert W M
AU - Martin, Victor S.
AU - Takatani, Muneo
AU - Viti, Steven M.
AU - Walker, Frederick J.
AU - Woodard, Scott S.
N1 - Funding Information:
Two very important aspects of these asymmetric epoxidations which have been ignored in this lecture are: 1) the mechanism of the process; and 2) the practical experimental details which facilitate execution of the process in the laboratory. These two subjects will be covered extensively in a review scheduled to aooear durinn Auqust of 1983 in Volume 16 (Issue No. 3) of Aldrichimica Acta.48'50 Acknowledgment. We thank the National Institutes of Health, the National Science Foundation, and Eli Lilly and Company for generous financial support.
PY - 1983/1
Y1 - 1983/1
N2 - A diverse selection of new synthetic applications of the titanium-catalyzed asymmetric epoxidation (AE) process is described. These include asymmetric syntheses of (+)-Darvon Alcohol, (-)-bestatin, (+)-2-methyl bestatin, (-)-propranolol, (-)-α-amino-β-hydroxybutyric acid, and (-)- and (+)-frontal in. The kinetic resolution mode of the AE process was used to prepare chiral insect pheromones in very high (>99% e.e.) optical purity; these include (+)-and (-)-a-caprolactone, (-)-exobrevicomin, (-)-endobrevi-comin, (+)-and (-)-ipsdienol, and (+)-trans-verbenol. A number of unusual kinetic resolutions based on the AE process are presented; these include resolutions of allenic alcohols, α-acetylenic carbinols, β-hydroxy sulfides, and a dienol.
AB - A diverse selection of new synthetic applications of the titanium-catalyzed asymmetric epoxidation (AE) process is described. These include asymmetric syntheses of (+)-Darvon Alcohol, (-)-bestatin, (+)-2-methyl bestatin, (-)-propranolol, (-)-α-amino-β-hydroxybutyric acid, and (-)- and (+)-frontal in. The kinetic resolution mode of the AE process was used to prepare chiral insect pheromones in very high (>99% e.e.) optical purity; these include (+)-and (-)-a-caprolactone, (-)-exobrevicomin, (-)-endobrevi-comin, (+)-and (-)-ipsdienol, and (+)-trans-verbenol. A number of unusual kinetic resolutions based on the AE process are presented; these include resolutions of allenic alcohols, α-acetylenic carbinols, β-hydroxy sulfides, and a dienol.
UR - https://www.scopus.com/pages/publications/0020112101
U2 - 10.1351/pac198855040589
DO - 10.1351/pac198855040589
M3 - Journal article
AN - SCOPUS:0020112101
SN - 0033-4545
VL - 55
SP - 589
EP - 604
JO - Pure and Applied Chemistry
JF - Pure and Applied Chemistry
IS - 4
ER -