Formation of chiral tertiary homoallylic alcohols via Evans aldol reaction or enzymatic resolution and their influence on the Sharpless asymmetric dihydroxylation

Tetrahedron ◽  
2010 ◽  
Vol 66 (21) ◽  
pp. 3814-3823 ◽  
Author(s):  
Matthias Theurer ◽  
Peter Fischer ◽  
Angelika Baro ◽  
Giang Son Nguyen ◽  
Robert Kourist ◽  
...  
Keyword(s):  
Aldol Reaction ◽  
Enzymatic Resolution ◽  
Asymmetric Dihydroxylation ◽  
Homoallylic Alcohols

ChemInform Abstract: Formation of Chiral Tertiary Homoallylic Alcohols via Evans Aldol Reaction or Enzymatic Resolution and Their Influence on the Sharpless Asymmetric Dihydroxylation.

ChemInform ◽  
2010 ◽  
Vol 41 (39) ◽  
pp. no-no
Author(s):  
Matthias Theurer ◽  
Peter Fischer ◽  
Angelika Baro ◽  
Giang Son Nguyen ◽  
Robert Kourist ◽  
...  
Keyword(s):  
Aldol Reaction ◽  
Enzymatic Resolution ◽  
Asymmetric Dihydroxylation ◽  
Homoallylic Alcohols

Synthesis of the C19–C30 Bis-THF Fragment of Iriomoteolide-13a via Stepwise SN2 Cyclization and Intramolecular syn-Oxypalladation

2020 ◽  
Author(s):  
Hui Zhao ◽  
Kai Gao ◽  
Haichen Ma ◽  
Tsz Chun Yip ◽  
Wei-Min Dai
Keyword(s):  
Aldol Reaction ◽  
Allylic Alcohol ◽  
Asymmetric Dihydroxylation ◽  
Hydroxy Groups

The C19–C30 bis-THF fragment of the proposed structure of iriomoteolide-13a has been synthesized. The w-mesyloxy-substituted stereotetrad possessing three continuous hydroxy groups was generated by <i>anti</i>-aldol reaction and asymmetric dihydroxylation (AD). Upon heating in pyridine the stereotetrad underwent an S<sub>N</sub>2 cyclization to form the C19–C22 THF ring. It was followed by an intramolecular <i>syn</i>-oxypalladation of the C28 chiral allylic alcohol to give the C23–C26 THF ring.

The asymmetric dihydroxylation of cis-allylic and homoallylic alcohols

1994 ◽  
Vol 35 (6) ◽  
pp. 843-846 ◽  
Author(s):  
Michael S. VanNieuwenhze ◽  
K.Barry Sharpless
Keyword(s):  
Asymmetric Dihydroxylation ◽  
Homoallylic Alcohols

Synthesis of the C19–C30 Bis-THF Fragment of Iriomoteolide-13a via Stepwise SN2 Cyclization and Intramolecular syn-Oxypalladation

2020 ◽  
Author(s):  
Hui Zhao ◽  
Kai Gao ◽  
Haichen Ma ◽  
Tsz Chun Yip ◽  
Wei-Min Dai
Keyword(s):  
Aldol Reaction ◽  
Allylic Alcohol ◽  
Asymmetric Dihydroxylation ◽  
Hydroxy Groups

The C19–C30 bis-THF fragment of the proposed structure of iriomoteolide-13a has been synthesized. The w-mesyloxy-substituted stereotetrad possessing three continuous hydroxy groups was generated by <i>anti</i>-aldol reaction and asymmetric dihydroxylation (AD). Upon heating in pyridine the stereotetrad underwent an S<sub>N</sub>2 cyclization to form the C19–C22 THF ring. It was followed by an intramolecular <i>syn</i>-oxypalladation of the C28 chiral allylic alcohol to give the C23–C26 THF ring.

Synthesis of the C19–C30 Bis-THF Fragment of Iriomoteolide-13a via Stepwise SN2 Cyclization and Intramolecular syn-Oxypalladation

2021 ◽  
Author(s):  
Hui Zhao ◽  
Kai Gao ◽  
Haichen Ma ◽  
Tsz Chun Yip ◽  
Wei-Min Dai
Keyword(s):  
Aldol Reaction ◽  
Asymmetric Dihydroxylation ◽  
Hydroxy Groups

The C19–C30 bis-THF fragment of the proposed structure of iriomoteolide-13a has been synthesized. The ω-mesyloxy-substituted stereotetrad possessing three continuous hydroxy groups was generated by anti-aldol reaction and asymmetric dihydroxylation (AD)...

scholarly journals A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols

Molecules ◽  
2016 ◽  
Vol 21 (7) ◽  
pp. 842 ◽  
Author(s):  
Xufeng Hou ◽  
Zhenzhong Jing ◽  
Xiangbin Bai ◽  
Zhiyong Jiang
Keyword(s):  
Aldol Reaction ◽  
One Pot ◽  
Homoallylic Alcohols ◽  
Catalytic Asymmetric

Reconstruction of Carbon Bond Frameworks via Oxapalladacycle Promoted by Synergistic Effect of Palladium Catalyst and Triethylborane

Synthesis ◽  
2021 ◽  
Author(s):  
Ryo Ninokata ◽  
Riho Korogi ◽  
Junya Nakao ◽  
Tsutomu Fukuda ◽  
Gen Onodera ◽  
...  
Keyword(s):  
Synergistic Effect ◽  
Palladium Catalyst ◽  
Aldol Reaction ◽  
Conjugated Dienes ◽  
Prins Reaction ◽  
Carbon Bond ◽  
Unsaturated Aldehydes ◽  
Homoallylic Alcohols ◽  
Diastereomeric Mixture

Pd-catalyzed β-carbon elimination of 3-hydroxy-4-pentenoic acid derivatives promoted by triethylborane proceeded to form conjugated dienes via a decarboxylation process. The formed conjugated dienes underwent the Prins reaction with aldehydes in situ to afford conjugated homoallylic alcohols. These sequential transformations enabled conversion of a diastereomeric mixture of 3-hydroxy-4-pentenoic acids, which were readily prepared from the simple crossed aldol reaction of esters and α,β-unsaturated aldehydes, to 3,5-hexadienyl alcohols with high regio- and stereoselectivities in a single manipulation.

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