Enantioselective Addition Of Arylboronic Acids Research Articles

ChemInform Abstract: Rhodium‐Catalyzed Highly Enantioselective Addition of Arylboronic Acids to 2‐Nitrostyrenes by tert‐Butanesulfinylphosphine Ligand.

AbstractBased on the title method, the first asymmetric synthesis of cherylline (VI) is reported.

Rhodium‐Catalyzed Highly Enantioselective Addition of Arylboronic Acids to 2‐Nitrostyrenes by tert‐Butanesulfinylphosphine Ligand

Particularly picky ligands! An efficient (S/C, substrate/catalyst, up to 500) Rh-catalyzed enantioselective addition of arylboronic acids to 2-nitrostyrenes under mild conditions was developed, which gave excellent yields (up to 99 %) and enantioselectivities (up to 98 % ee) by using tert-butanesulfinylphosphine as a ligand (see scheme). Based on this method, (R)-cherylline was synthesized in 70 % overall yield. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Synthesis of aryl(ferrocenyl)methanols via an enantioselective addition of arylboronic acids

Enantiomerically enriched ferrocenyl alcohols are important intermediates in the synthesis of a range of chiral ferrocene-derived ligands. We studied various possibilities for their synthesis by the catalytic enantioselective addition of arylboronic acids to ferrocenyl carbonyl compounds. The best system comprised of ferrocenyl oxazolinyl alcohol as a catalyst and an arylation reagent generated from a boronic acid and diethylzinc. Aryl ferrocenyl methanols were synthesized in yields of up to 97% and with enantiomeric purities of up to er 98:2.

Asymmetric Rhodium-Catalyzed Addition of Arylboronic Acids to Alkenylheteroarenes

In this paper the authors report the first catalytic enantioselective addition of arylboronic acids and alkenyl N-methyliminodiacetic acid (MIDA) boronate to β-substituted alkenyl­heteroarenes. Various types of substrates were employed, containing π-deficient quinoline, quin­oxaline, pyrimidine moieties as well as π-excessive oxazole and oxadiazole fragments; the products were obtained in 56-91% yields and with 89-98% ee. Introduction of the alkenyl moiety could be ­accomplished via alkenyl MIDA boronates. Microwave irradiation could be replaced by thermal heating.

A chiral Rh–phosphite complex displaying high activity in the enantioselective Rh-catalyzed addition of arylboronic acids to carbonyl compounds: when and why atropos is better than tropos

The use of deoxycholic acid derived tropos and atropoisomeric phosphites as chiral ligands in the Rh-catalyzed enantioselective addition of arylboronic acids to arylaldehydes and 2,2,2-trifluoroacetophenone is presented. Screening of these phosphites showed the high activity of the Rh-complex obtained starting from one of the two atropoisomeric ligands, which afforded complete conversion of the carbonyl compounds in short reaction times under mild reaction conditions and with ee’s of up to 84%. A study aimed at getting information about the different behavior of tropos and atropoisomeric ligands is also reported.

An N‐Linked Bidentate Phosphoramidite Ligand (N‐Me‐BIPAM) for Rhodium‐Catalyzed Asymmetric Addition of Arylboronic Acids to N‐Sulfonylarylaldimines

AbstractA chiral N‐linked C2‐symmetric bidentate phosphoramidite (N‐Me‐BIPAM) was newly developed for the rhodium‐catalyzed enantioselective addition of arylboronic acids to N‐sulfonylimines. This ligand achieved high enantioselectivities in a range of 84–99% ee in additions of arylboronic acids to N‐tosyl‐ and N‐nosylarylaldimines.

Rh-Catalyzed Enantioselective Addition of Arylboronic Acids to Aliphatic Imines

The enantioselective catalytic addition of arylboronic acids to aliphatic imines is reported. The corresponding α-aryl alkylamines are obtained with excellent yields and enantioselectivities. This work represents one of the few examples of boronic acid addition to aliphatic imines.

Enantioselective Addition of Arylboronic Acids to a-Keto Esters

Enantioselective Addition of Arylboronic Acids to a-Keto Esters

ChemInform Abstract: Catalytic Enantioselective Addition of Arylboronic Acids to N‐Boc Imines Generated in situ.

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Catalytic Enantioselective Addition of Arylboronic Acids to N-Boc Imines Generated in Situ

The rhodium-catalyzed addition of arylboronic acids to N-Boc imines generated in situ from stable and easily prepared alpha-carbamoyl sulfones has been developed. High enantioselectivities are observed for additions of arylboronic acids with a variety of steric and electronic properties.