Synthesis of 1,4- and 1,5-Amino Alcohols via Nucleophilic Addition of Semicyclic N,O-Acetal with Organozinc Reagents

2019 ◽  
Vol 84 (17) ◽  
pp. 11261-11267 ◽  
Author(s):  
Xue-Mei Wang ◽  
Yi-Wen Liu ◽  
Rui-Jun Ma ◽  
Chang-Mei Si ◽  
Bang-Guo Wei
Keyword(s):  
Nucleophilic Addition ◽  
Amino Alcohols ◽  
Organozinc Reagents

Synthesis of 1-benzylisoindoline and 1-benzyl-tetrahydroisoquinoline through nucleophilic addition of organozinc reagents to N,O-acetals

2020 ◽  
Vol 18 (36) ◽  
pp. 7139-7150
Author(s):  
Rui-Jun Ma ◽  
Jian-Ting Sun ◽  
Chang-Hong Liu ◽  
Ling Chen ◽  
Chang-Mei Si ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
New Approach ◽  
Organozinc Reagents

A new approach to access 1-benzylisoindoline and 1-benzyl-tetrahydroisoquinoline has been developed through nucleophilic addition of organozinc reagents to N,O-acetals.

scholarly journals Applications of tert-butanesulfinamide in the asymmetric synthesis of amines

2003 ◽  
Vol 75 (1) ◽  
pp. 39-46 ◽  
Author(s):  
J. A. Ellman
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Amino Alcohols ◽  
Wide Range ◽  
Aldehydes And Ketones ◽  
Directing Group ◽  
High Yields ◽  
Direct Condensation

tert-Butanesulfinamide is prepared using catalytic enantioselective methods in two steps from the extremely inexpensive oil waste by-product, tert-butyl disulfide. Direct condensation of tert-butanesulfinamide with aldehydes and ketones provides tert-butanesulfinyl imines in uniformly high yields. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched and α,α-dibranched amines, α- and β-amino acids, 1,2 and 1,3-amino alcohols and α-trifluoromethyl amines are efficiently synthesized using this methodology.

Chelation Controlled Nucleophilic Addition of Tetraoric Acid Dianion to Aldimines: Towards the Stereoselective Construction of b-Amino Alcohols

Heterocycles ◽  
1993 ◽  
Vol 35 (2) ◽  
pp. 671 ◽  
Author(s):  
Toshio Honda ◽  
Tomohisa Hayakawa ◽  
Toshio Yamada ◽  
Hirotsune Kondoh ◽  
Hiromasa Nagase
Keyword(s):  
Nucleophilic Addition ◽  
Amino Alcohols

scholarly journals Nucleophilic Addition of Organozinc Reagents to 2-Sulfonyl Cyclic Ethers: Stereoselective Synthesis of Manassantins A and B

2009 ◽  
Vol 11 (7) ◽  
pp. 1671-1671
Author(s):  
Hyoungsu Kim ◽  
Amanda C. Kasper ◽  
Eui Jung Moon ◽  
Yongho Park ◽  
Ceshea M. Wooten ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Stereoselective Synthesis ◽  
Cyclic Ethers ◽  
Organozinc Reagents

Magnesium salt promoted tandem nucleophilic addition–Oppenauer oxidation of aldehydes with organozinc reagents

2016 ◽  
Vol 14 (41) ◽  
pp. 9720-9724 ◽  
Author(s):  
Ying Fu ◽  
Xing Ling Zhao ◽  
Hulmet Hügel ◽  
Danfeng Huang ◽  
Zhengyin Du ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Aromatic Aldehydes ◽  
Magnesium Salt ◽  
Facile Synthesis ◽  
Aromatic Ketones ◽  
Oppenauer Oxidation ◽  
Organozinc Reagents

A facile synthesis of aromatic ketones via tandem nucleophilic addition–Oppenauer oxidation of aromatic aldehydes with organozinc reagents was demonstrated. Magnesium salt in situ generated via organozinc formation is a powerful promotor for this transformation.

Highly diastereoselective synthesis of 1,2-amino alcohols via nucleophilic addition of organocerium reagents to 4- and 5-oxazolidinonecarbaldehydes

1998 ◽  
Vol 76 (7) ◽  
pp. 1070-1081 ◽  
Author(s):  
Andrew GH Wee ◽  
Fuxing Tang
Keyword(s):  
Nucleophilic Addition ◽  
Amino Alcohols ◽  
Diastereoselective Synthesis

The reaction of chiral, non-racemic 4- and 5-oxazolidinonecarbaldehydes, 6 and 13, with organocerium reagents proceeds efficiently with good to excellent diastereoselectivity to give syn and anti alcohols, respectively. A model to explain the observed diastereoselectivity of the reaction of 6 and 13 is provided. The utility of this method for the synthesis of amino alcohols is exemplified by the synthesis of C-18-D-ribo-phytosphingosine from the anti alcohol 14f.Key words: oxazolidinonecarbaldehydes, organocerium, diastereoselective, amino alcohols, C-18-ribo-phytospingosine.

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