Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol.

Literature DB >> 20476769

Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol.

Abstract

Delta-methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z >30:1 and 93% to >95% ee via BF(3).Et(2)O-promoted allylboration with alpha-Me-allylboronate 1. The origin of high (E)-selectivity is proposed.

Entities: CellLine Chemical Disease Gene

Mesh：

Substances：

Year: 2010 PMID： 20476769 PMCID： PMC2891445 DOI： 10.1021/ol1007444

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

48 in total

1. The first and highly enantioselective crotylation of aldehydes via an allyl-transfer reaction from a chiral crotyl-donor.

Authors: J Nokami; M Ohga; H Nakamoto; T Matsubara; I Hussain; K Kataoka
Journal: J Am Chem Soc Date: 2001-09-19 Impact factor: 15.419

2. Highly enantioselective Alk-2-enylation of aldehydes through an allyl-transfer reaction.

Authors: Junzo Nokami; Kenta Nomiyama; Seiji Matsuda; Nobuyuki Imai; Kazuhide Kataoka
Journal: Angew Chem Int Ed Engl Date: 2003-03-17 Impact factor: 15.336

3. Synthesis of the C1-C21 Fragment of the Serine/Threonine Phosphatase Inhibitor Tautomycin.

Authors: Karl W. Maurer; Robert W. Armstrong
Journal: J Org Chem Date: 1996-05-03 Impact factor: 4.354

4. New route to alpha-adducts of homoallylic alcohols by an acid-catalyzed stereospecific allyl-transfer reaction from gamma-adducts

Authors:
Journal: Chemistry Date: 2000-08-18 Impact factor: 5.236

5. Acceleration effect of Lewis acid in allylboration of aldehydes: catalytic, regiospecific, diastereospecific, and enantioselective synthesis of homoallyl alcohols.

Authors: Tatsuo Ishiyama; Taka-aki Ahiko; Norio Miyaura
Journal: J Am Chem Soc Date: 2002-10-23 Impact factor: 15.419

6. Dramatic rate enhancement with preservation of stereospecificity in the first metal-catalyzed additions of allylboronates.

Authors: Jason W J Kennedy; Dennis G Hall
Journal: J Am Chem Soc Date: 2002-10-02 Impact factor: 15.419

7. Synthesis of the C22-C26 tetrahydropyran segment of phorboxazole by a stereoselective prins cyclization

Authors:
Journal: Org Lett Date: 2000-05-04 Impact factor: 6.005

8. Development of a highly alpha-regioselective metal-mediated allylation reaction in aqueous media: new mechanistic proposal for the origin of alpha-homoallylic alcohols.

Authors: Kui-Thong Tan; Shu-Sin Chng; Hin-Soon Cheng; Teck-Peng Loh
Journal: J Am Chem Soc Date: 2003-03-12 Impact factor: 15.419

9. Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of beta-substituted alpha-amino acid derivatives.

Authors: Martin J O'Donnell; Jeremy T Cooper; Mary M Mader
Journal: J Am Chem Soc Date: 2003-03-05 Impact factor: 15.419

10. The first example of enantioselective allyl transfer from a linear homoallylic alcohol to an aldehyde.

Authors: Teck-Peng Loh; Chi-Lik Ken Lee; Kui-Thong Tan
Journal: Org Lett Date: 2002-08-22 Impact factor: 6.005

10 in total

1. Cationic tricoordinate boron intermediates: borenium chemistry from the organic perspective.

Authors: Timothy S De Vries; Aleksandrs Prokofjevs; Edwin Vedejs
Journal: Chem Rev Date: 2012-04-20 Impact factor: 60.622

2. A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

Authors: Ryan J Morrison; Farid W van der Mei; Filippo Romiti; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2019-12-24 Impact factor: 15.419

3. Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates.

Authors: Qi Zhou; Harathi D Srinivas; Songnan Zhang; Mary P Watson
Journal: J Am Chem Soc Date: 2016-09-02 Impact factor: 15.419

4. Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.

Authors: Philippe Nuhant; Jeremy Kister; Ricardo Lira; Achim Sorg; William R Roush
Journal: Tetrahedron Date: 2011-09-02 Impact factor: 2.457

5. Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin-Hammett controlled double asymmetric crotylboration reactions of (S)-E-αphenyldimethylsilyl( ^d diisopinocampheyl)-crotylborane.

Authors: Ming Chen; William R Roush
Journal: Tetrahedron Date: 2013-09-09 Impact factor: 2.457

6. Enantiodivergent Hydroboration Reactions of a Racemic Allenylsilane with Diisopinocampheylborane and Curtin-Hammett Controlled Double Asymmetric Crotylboration Reactions of (S)-E-α-phenyldimethylsilyl( ^d diisopinocampheyl)-crotylborane.

Authors: Ming Chen; William R Roush
Journal: Tetrahedron Date: 2013-07-01 Impact factor: 2.457

7. Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.

Authors: Ming Chen; William R Roush
Journal: J Am Chem Soc Date: 2013-06-12 Impact factor: 15.419