3238-63-9Relevant academic research and scientific papers
Asymmetric synthesis and structural assignment of (-)-α-conhydrine
Enders, Dieter,Nolte, Bert,Raabe, Gerhard,Runsink, Jan
, p. 285 - 291 (2002)
The first asymmetric synthesis of the conium alkaloid (-)-α-conhydrine is reported. Starting from a protected glycol aldehyde hydrazone as chiral precusor, a short route based on our α-alkylation/1,2-addition methodology has been developed. After cleavage of the auxiliary and simultaneous deprotection, the concluding ring closure is accomplished under reductive amination conditions. The title compound is obtained in moderate overall yield and in excellent diastereo- and enantiomeric excess (d.e., e.e. >96%). Single-crystal X-ray crystallography as well as 1H NMR NOE experiments confirm the expected relative and absolute (2R,7S)-configuration of the product.
Stereoselective synthesis of (-)-α-conhydrine and its pyrrolidine analogue
Dong, Guang Ri,Hong, Seungmin,Kim, Seung In,Kim, In Su,Jung, Young Hoon
, p. 4200 - 4205 (2012/10/07)
The stereoselective synthesis of (-)-α-conhydrine and its pyrrolidine analogue was achieved from readily available D-erythronolactone. The key step of this synthesis includes a highly regioselective and diastereoselective addition of chlorosulfonyl isocyanate to 1,2-anti-dibenzyl ether to afford the 1,2-anti-amino alcohol. The total synthesis of (-)-α-conhydrine and its pyrrolidine analogue starting from readily available D-erythronolactone was achieved via the regioselective and diastereoselective allylic amination of anti-1,2-dibenzyl ether by using chlorosulfonyl isocyanate.
A straightforward synthesis of conhydrine by hetero Diels-Alder strategy mediated by microwaves
Bandini, Elisa,Corda, Giulia,D'Aurizio, Antonio,Panunzio, Mauro
supporting information; experimental part, p. 933 - 934 (2010/05/18)
Synthesis of optically active conhydrines has been achieved by hetero Diels-Alder cycloaddition assisted by microwaves.
Highly enantioselective synthesis of chiral cyclic amino alcohols and conhydrine by ruthenium-catalyzed asymmetric hydrogenation
Liu, Sheng,Xie, Jian-Hua,Li, Wei,Kong, Wei-Ling,Wang, Li-Xin,Zhou, Qi-Lin
supporting information; experimental part, p. 4994 - 4997 (2009/12/28)
A highly efficient enantio- and diastereoselective synthesis of chiral cis-β-N-alkyl/arylamino cyclic alcohols has been realized by asymmetric hydrogenation of racemic α-amino cyclic ketones via DKR catalyzed by [RuCl2((S)-Xyl-SDP)((R,R)-DPEN)]. The enantioselectivities of the reaction were up to 99.9% ee with 99:1 cis-selectivities. A practical catalytic asymmetric synthesis of all four isomers of conhydrine was also developed.
Short and efficient asymmetric synthesis of (-)-α-conhydrine
Voituriez, Arnaud,Ferreira, Franck,Chemla, Fabrice
, p. 5358 - 5361 (2008/02/08)
(Chemical Equation Presented) The short and efficient synthesis of (-)-α-conhydrine was accomplished with 41% overall yield in seven steps and high diastereo- and enantioselectivity. The anti-stereochemistry of the two stereogenic centers has been confirmed by the single-crystal X-ray analysis of an intermediate.
Asymmetric synthesis of (-)-α-conhydrine
Kandula, Subba Rao V.,Kumar, Pradeep
, p. 3268 - 3274 (2007/10/03)
The enantioselective synthesis of (-)-α-conhydrine has been achieved by two different synthetic routes. The key steps include Sharpless asymmetric dihydroxylation, regioselective opening of a cyclic sulfate and Wittig olefination.
Enantioselective synthesis of (-)-α-conhydrine via cyclic sulfate methodology
Kandula, SubbaRao V.,Kumar, Pradeep
, p. 1957 - 1958 (2007/10/03)
An asymmetric synthesis of (-)-α-conhydrine is described using the Sharpless asymmetric dihydroxylation and the regiospecific nucleophilic opening of a cyclic sulfate as the key steps.
