Organocatalytic Diastereoselective (4 + 1) Cycloaddition of o-Hydroxyphenyl-Substituted Secondary Phosphine Oxides DOI
Shufang Wu,

Guo‐Ke Zhang,

Xue Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16497 - 16510

Опубликована: Ноя. 20, 2023

The first organocatalytic diastereoselective (4 + 1) cycloaddition of o-hydroxyphenyl-substituted secondary phosphine oxides (SPOs) has been established, which makes use o-hydroxyphenyl substituted SPOs as suitable four-atom phosphorus-containing 1,4-dinucleophiles and 3-indolylformaldehydes competent 1,1-dielectrophiles under Bro̷nsted acid catalysis. reaction mechanism was suggested to involve the formation 3-indolylmethanol intermediates vinyliminium intermediates, played an important role in controlling reactivity diastereoselectivity By this approach, a series benzo oxaphospholes bearing P- C-stereocenters were synthesized moderate good yields (50%-95% yields) with excellent diastereoselectivities (all >95:5 dr). This not only represents but also provides efficient method for construction five-membered heterocyclic skeletons both P-stereocenter C-stereocenter.

Язык: Английский

Stereospecific Phosphination and Thioetherification of Organoboronic Esters DOI
Hao Liang, Michael R. Berwanger, James P. Morken

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(28), С. 18873 - 18878

Опубликована: Июль 2, 2024

Alkyllithium-activated organoboronic esters are found to undergo stereospecific phosphination with copper chloride and chlorophosphines. They also react thiolsulfonate electrophiles under catalysis. These reactions enable thiolation of esters, which further applied in preparation chiral ligands biologically active molecules.

Язык: Английский

Процитировано

3
Rhodium-catalyzed enantioselective hydrogenation of (1-arylvinyl)phosphonates with TADDOL-based phosphoramidite P,S ligands DOI
Vladislav S. Zimarev, Ilya D. Firsin, A. V. Larin

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An efficient synthesis of chiral (1-arylethyl)phosphonates practical interest is reported via asymmetric hydrogenation α,β-unsaturated precursors using a novel Rh( i )-catalyst.

Язык: Английский

Процитировано

0
Organocatalytic Diastereoselective (4 + 1) Cycloaddition of o-Hydroxyphenyl-Substituted Secondary Phosphine Oxides DOI
Shufang Wu,

Guo‐Ke Zhang,

Xue Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16497 - 16510

Опубликована: Ноя. 20, 2023

The first organocatalytic diastereoselective (4 + 1) cycloaddition of o-hydroxyphenyl-substituted secondary phosphine oxides (SPOs) has been established, which makes use o-hydroxyphenyl substituted SPOs as suitable four-atom phosphorus-containing 1,4-dinucleophiles and 3-indolylformaldehydes competent 1,1-dielectrophiles under Bro̷nsted acid catalysis. reaction mechanism was suggested to involve the formation 3-indolylmethanol intermediates vinyliminium intermediates, played an important role in controlling reactivity diastereoselectivity By this approach, a series benzo oxaphospholes bearing P- C-stereocenters were synthesized moderate good yields (50%-95% yields) with excellent diastereoselectivities (all >95:5 dr). This not only represents but also provides efficient method for construction five-membered heterocyclic skeletons both P-stereocenter C-stereocenter.

Язык: Английский

Процитировано

3