Chiral phosphoric acid for allenamides with ketones

Dean Toste and colleague have reported in Chemical Science on the use of a chiral phosphoric acid catalyst to react allenamides with ketones. I guess the papers published in Chemical Science in 2015 and 2016 are all open access.

 

Chemical Science paper

Jungermannenones B and C synthesis

Xiaoguang Lei and co-workers from Peking University have reported in ACIE on the synthesis of jungermannenones B and C.

 

ACIE paper

3 Diels-Alder reactions in 1 go

Michael Sherburn and co-workers from the Australian National University reported in JOC on a Diels-Alder cascade sequence.

JOC paper

 

Here’s an interesting related ACIE paper by the same group.

2 Reagents, 2 mechanisms, same product

Srinivasan Chandrasekaran and colleague at the Indian Institute of Science have reported in Tetrahedron on a mechanistically interesting transformation involving a geminal aminooxygenation of a vinyl arene. Two different reaction conditions were identified: one with m-CPBA, the other with a hypervalent iodine reagent. The former underwent a deuterium shift on the gem-dideuterated-styrene starting material and the latter does not.

Tetrahedron paper

Expect the unexpected – allylic alcohols from epoxides

Margaret Brimble and co-workers from the University of Auckland have reported in Organic Letters on a cobalt-catalyzed conversion of an epoxide to an allylic alcohol using the Corey-Chaykovsky reagent.

 

OL paper

Alkyne hydrothiolation with Wilkinson’s catalyst

Jennifer Love and co-workers from the University of British Columbia reported in Organic Letters on the use of Wilkinson’s catalyst to perform a hydrothiolation reaction across an alkyne to synthesize K777, a cysteine protease inhibitor.

 

OL paper

Fusarisetin A synthesis

Yandong Zhang and co-workers at Xiamen University have reported in Organic Letters on a synthesis of fusarisetin A using a one pot intramolecular Diels-Alder/Mukaiyama aldol reaction cascade sequence.

OL paper

Vesparioside B synthesis

Jin-Song Yang and co-workers from Sichuan University have reported in JACS on the synthesis of vesparioside B.

 

JACS paper

Ileabethoxazole, Pseudopteroxazole, and seco-Pseudopteroxazole syntheses

Ang Li and co-workers from SIOC have reported in ACIE on the syntheses of three diterpenoids.

 

ACIE paper

From carboxylic acid to ketone

Peter Schreiner and co-workers from Justus-Liebig University have reported in ACIE on an asymmetric Dakin-West reaction. I am reminded of a similar transformation from carboxylic acid chlorides to trifluoroketones reported by Samir Zard’s group. From my own experience, the Zard reaction also works with just a carboxylic acid as the starting material (except, as pointed out – is not an asymmetric reaction).

 

ACIE paper