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1 article(s) from Malik, Michał

syn-dihydroxylation

Michał Malik and
Sławomir Jarosz

Beilstein J. Org. Chem. 2016, 12, 2602–2608, doi:10.3762/bjoc.12.255

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Graphical Abstract

Figure 1: General structures of mono- and bicyclic carbasugars.

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Scheme 1: Approach to the synthesis of bicyclic carbasugars based on the use of sugar allyltins (previous wor...

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Scheme 2: Approach to the synthesis of bicyclic decalins based on a 1,4-addition/aldol reaction followed by R...

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Scheme 3: Reagents and conditions: (a) i. Zn, MeOH/H₂O, 60 °C, 2 h, ii. Jones reagent, acetone, rt, 1 h, iii....

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Scheme 4: Reagents and conditions: (a) i. BzCl, DCM, Et₃N, DMAP, rt, 24 h, ii. HCl, MeOH/H₂O, rt, 24 h, 55% (...

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Scheme 5: Reagents and conditions: (a) TBAF∙3H₂O, THF, rt, 24 h, 96% (19) or 94% (23); (b) i. BzCl, DCM, Et₃N...

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Scheme 6: Reagents and conditions: (a) vinyl-MgBr, CuBr∙Me₂S, THF, −45 °C, 15 min, then (S)- or (R)-10, −45 °...

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Scheme 7: Reagents and conditions: (a) Hoveyda–Grubbs II cat. (5 mol %), toluene, 50 °C, 2 h, then evaporatio...

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Figure 2: Possible course of the syn-dihydroxylation leading to 27, 28, and 29.

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Scheme 8: Reagents and conditions: (a) NaBH(OAc)₃, MeCN/THF/AcOH, rt, 24 h, 67% (30, dr >99:1) or 74% (31 + 32...

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Published 01 Dec 2016

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