Scope of the directed dihydroxylation: application to cyclic homoallylic alcohols and trihaloacetamides.

Scope of the directed dihydroxylation: application to cyclic homoallylic alcohols and trihaloacetamides.

The synthesis and directed dihydroxylation of a range of cyclic alkenes was investigated. Both homoallylic alcohols and homoallylic trihaloacetamides were found to be efficient directing groups, giving rise to good to excellent levels of remote asymmetric induction with OsO4-TMEDA. Interestingly, in...

Full description

Bibliographic Details
Main Authors:	Donohoe, T, Mitchell, L, Waring, M, Helliwell, M, Bell, A, Newcombe, N
Format:	Journal article
Language:	English
Published:	2003

Similar Items

Homoallylic alcohols and trichloroacetamides as hydrogen bond donors for directed dihydroxylation
by: Donohoe, T, et al.
Published: (2001)

The directed dihydroxylation of allylic alcohols
by: Donohoe, T, et al.
Published: (1997)

Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA.
by: Donohoe, T, et al.
Published: (2002)

syn stereocontrol in the directed dihydroxylation of acyclic allylic alcohols
by: Donohoe, T, et al.
Published: (1999)

The directed dihydroxylation of allylic alcohols.
by: Waring, M, et al.
Published: (1999)

Enhanced stereoselectivity in the catalytic dihydroxylation of acyclic allylic alcohols
by: Donohoe, T, et al.
Published: (2000)

On the dihydroxylation of cyclic allylic alcohols
by: Donohoe, T, et al.
Published: (1996)

Directed dihydroxylation of allylic trichloroacetamides
by: Donohoe, T, et al.
Published: (1999)

Synthesis of amino-sugars using the directed dihydroxylation reaction
by: Donohoe, T, et al.
Published: (1999)

Development of the directed dihydroxylation reaction
by: Donohoe, T
Published: (2002)

Studies on the role of conformation and of hydrogen-bonding on the dihydroxylation of cyclic allylic alcohols: Application to the synthesis of conduritol D
by: Donohoe, T, et al.
Published: (1997)

Ammonium-directed oxidation of cyclic allylic and homoallylic amines.
by: Bond, C, et al.
Published: (2009)

Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines
by: Kurosawa, W, et al.
Published: (2010)

Osmium-free direct syn-dihydroxylation of alkenes.
by: Bataille, C, et al.
Published: (2011)

Hydrogen-bonding-mediated directed osmium dihydroxylation
by: Donohoe, T, et al.
Published: (2011)

A syn selective dihydroxylation of cyclic allylic trichloroacetamides using catalytic osmium tetroxide
by: Blades, K, et al.
Published: (2000)

Iodine-Catalyzed Prins Cyclization of Homoallylic Alcohols and Aldehydes
by: Luiz F. Silva, et al.
Published: (2013-09-01)

Syn-syn dihydroxylation of allylic amides.
by: Winter, J, et al.
Published: (2000)

Stereospecific synthesis of allylic and homoallylic alcohols from functionalized propargylic alcohols
by: Leiv K. Sydnes, et al.
Published: (2008-10-01)

One-pot conversions of olefins to cyclic carbonates and secondary allylic and homoallylic amines to cyclic carbamates.
by: Davies, S, et al.
Published: (2010)

An Investigation of the Reactions of Substituted Homoallylic Alcohols with Various Oxidation Reagents
by: A. Acar, et al.
Published: (2002-02-01)

Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene
by: Frederick J. Seidl, et al.
Published: (2016-07-01)

New osmium-based reagent for the dihydroxylation of alkenes.
by: Donohoe, T, et al.
Published: (2006)

Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes: development of a metal-free dihydroxylation protocol.
by: Aciro, C, et al.
Published: (2008)

The synthesis of (+)-pericosine B
by: Donohoe, T, et al.
Published: (1998)

Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation
by: Marcus V. Craveiro, et al.
Published: (2005-11-01)

Asymmetric organocatalytic synthesis of chiral homoallylic amines
by: Nikolay S. Kondratyev, et al.
Published: (2024-09-01)

Scope and limitations of the solution and solid phase synthesis of homoallylic amines via N-acyliminium ion reactions
by: W.J.N. Meester, et al.
Published: (2003-12-01)

A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols
by: Xufeng Hou, et al.
Published: (2016-06-01)

Dihydroxylation of butenol over bifunctional catalyst /
by: 291587 Yeow, Kian Wee, et al.
Published: (2006)

Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols
by: Rui Guo, et al.
Published: (2017-07-01)

Structural Characterization of Mono and Dihydroxylated Umbelliferone Derivatives
by: Rubén Seoane-Rivero, et al.
Published: (2020-07-01)

Photocatalytic dihydroxylation of light olefins to glycols by water
by: Chunyang Dong, et al.
Published: (2024-09-01)

Metal-free electrochemical dihydroxylation of unactivated alkenes
by: Min Liu, et al.
Published: (2023-10-01)

Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles
by: Peter Wipf, et al.
Published: (2011-06-01)

Synthesis and antifungal activity of N-aryl-N-benzylamines and of their homoallyl analogues
by: Francisco M. Garibotto, et al.
Published: (2011-02-01)

Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless Asymmetric Dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4
by: Richardson, M, et al.
Published: (2019)

Chiral Syn-1,3-diol Derivatives via a One-Pot Diastereoselective Carboxylation/ Bromocyclization of Homoallylic Alcohols
by: Guanxin Huang, et al.
Published: (2018-11-01)

Orthogonally Protected 1,2-Diols from Electron-Rich Alkenes Using Metal-Free Olefin syn-Dihydroxylation
by: Colomer Utrera, I, et al.
Published: (2016)

Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (-)-codonopsinine
by: Davies, S, et al.
Published: (2012)