Stereoselective Synthesis of Masked Amino‐polyols <i>via</i> Osmylation of 4,5‐Dihydro‐5‐vinylisoxazoles

Annunziata, Rita; Cinquini, Mauro; Cozzi, Franco; Raimondi, Laura; Restelli, A.

doi:10.1002/hlca.19850680518

Cited by 14 publications

(4 citation statements)

References 31 publications

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“…2-(2-Hydroxycyclopentylidene)ethanenitrile (1d). The general procedure was employed with 4d (117.3 mg in 1 mL of THF) followed by radial chromatography (2:3 EtOAc:hexanes) to provide 70.7 mg (60%) of 1d as an oil: IR (film) 2253, 3383 cm -1 ; 1 H NMR (CS 2 ) δ 1.83−2.10 (m, 2H), 2.21−2.31 (m, 1H), 2.37−2.46 (m, 2H), 2.92−3.00 (m, 2H), 4.74−4.78 (m, 1H), 5.70 (q, J = 2 Hz, 1H); 13 C NMR (CS 2 ) δ 22.2, 31.4, 36.5, 76.3, 93.9, 117.1, 173.2; MS m / e 124 (M + H). A hexanes solution of butyllithium (1.1 equiv, 1.45 M in hexanes) was added to a cold (−78 °C), THF solution (2 mL) of 1d (80.7 mg), followed after 10 min., by neat p -nitrobenzoyl chloride (134 mg).…”

Section: Methodsmentioning

confidence: 99%

Hydroxylated α,β-Unsaturated Nitriles: Stereoselective Synthesis

2001

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Section: Methodsmentioning

confidence: 99%

Hydroxylated α,β-Unsaturated Nitriles: Stereoselective Synthesis

2001

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“…In addition, an allylic oxygen substituent appears to retard the rate of asymmetric dihydroxylation. 95 Brimacombe examined the asymmetric dihydroxylation of the carbohydrate-derived a,/3-unsaturated esters (entries [30][31][32][33][34][35][36][37][38]. In matched examples (entries 31 and 34), the diastereoselectivity was enhanced.…”

Section: Double Stereodifferentiationmentioning

confidence: 99%

Acyclic Stereocontrol Induced by Allylic Alkoxy Groups. Synthetic Applications of Stereoselective Dihydroxylation in Natural Product Synthesis

Kun¹,

Kim²

1995

Chem. Rev.

186

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Jin K. Cha received a B.S. degree in chemistry from Seoul National University in 1975. In 1981, he received his D.Phil. degree from University of Oxford, England under the direction of Professor Jack E. Baldwin. The first two years of graduate study were spent at Massachusetts Institute of Technology. After a two-year period of postdoctoral training under Professor Yoshito Kishi at Harvard University, he joined the faculty at Vanderbilt University in 1983. In Fall 1991 he moved to the University of Alabama where he is currently Associate Professor of Chemistry. His research interests include the development and applications of new methods and strategies for natural product synthesis.No-Soo Kim was bom in Seoul, Korea, in 1957. He obtained a B.S. degree in industrial chemistry from Hanyang University, and a M.S. degree in organic chemistry from Korea Advanced Institute of Science. In 1992, he received his Ph.D. in organic chemistry under the direction of Professor James D. White at Oregon State University. His Ph.D. dissertation involved synthetic studies toward trichothecene. After a postdoctoral study at the University of Alabama with Professor J. K. Cha, he joined Youngdong Institute of Technology as an Assistant Professor in Spring 1994. His research interests include the synthesis of biologically active compounds.be exploited to exert a unique stereodirecting effect on adjacent prochiral sp2 sites. In addition, the ready availability of optically pure allylic alcohols by enantioselective reduction of the corresponding ketones lends itself to practical asymmetric synthesis.2'3

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“…Recovered starting material If was obtained as an oil. The product 7 (R1 = Meg(Me2CHCMeg)SiO(CH2)g) was also obtained as an oil; Rf 0.6 (20% ethyl acetate in hexane); [opD -17°(c 0.90, CHClg); NMR 6.88 (dd, J = 15.8 and 5.42 Hz, 1H), 5.92 (dd, J = 15.8 and 1.42 Hz, 1 H), 5.54 (m, 1 H), 3.73 (s, 3 H), 3.63 (m, 2 ), 2.08 (s, 3 ), 1.84 (m, 2 ), 0.89 (m, 1 ), 0.86 (d, J = 6.86 Hz, 6 ), 0.82 (s, 6 ), 0.06 (s, 6 H); 13C NMR 170.0 (C), 166.5 (C), 146.0 (CH/CHg), 120.9 (CH/CHg), 70.0 (CH/CHg), 58.3 (CHg), 51.8 (CH/CHg), 38.8 (CHg), 34.2 (CH/CHg), 25.1 (C), 21.0 (CH/CHg), 20.3 (CH/CHg), 18.5 (CH/CHg), -3.4 (CH/CHg), -3.5 (CH/CHg); IR (neat) 1745 (st), 1735 (st), 1665 (md) cm"1; MS (El, 30 eV) m/e (rel intensity) 309 (1), 307 (1), 271 (2), 117 (100); HRMS matched for [M -SiMe3]+ caled for C14Hgg06 271.15453, found 271.15492. Methyl 4-Acetoxy-5-methylhex-2-enoate (7, R1 = i-Pr).…”

Section: Reactions Of Methyl [(( )-4-chlorophenylmentioning

confidence: 99%