Literature DB >> 34870436

Soft Enolization of 3-Substituted Cycloalkanones Exhibits Significantly Improved Regiocontrol vs Hard Enolization Conditions.

Natalie C Dwulet1, Vincenzo Ramella1, Christopher D Vanderwal1,2.   

Abstract

Soft enolization conditions are revealed to be markedly better than the typically applied hard enolization protocols for regioselective enoxysilane formation from unsymmetrical 3-substituted cycloalkanones. Five-, six-, and seven-membered cycloalkanones each with 3-methyl, 3-isopropyl, or 3-phenyl substituents were investigated, and in all but one case, regioselectivities were ≥11:1 for enolization away from the substituent. These results are complementary to the regiospecific enoxysilane formation derived from cycloalkenone conjugate addition/enolate silylation.

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Year:  2021        PMID： 34870436      PMCID： PMC8766248          DOI： 10.1021/acs.orglett.1c03844

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


  8 in total

1.  Concise Formal Synthesis of the Pseudopterosins via Anionic Oxy-Cope/Transannular Michael Addition Cascade.

Authors:  Vincenzo Ramella; Philipp C Roosen; Christopher D Vanderwal
Journal:  Org Lett       Date:  2020-02-20       Impact factor: 6.005

2.  Synthetic Study toward Total Synthesis of (±)-Germine: Synthesis of (±)-4-Methylenegermine.

Authors:  Gilbert Stork; Ayako Yamashita; Robert M Hanson; Ly Phan; Eifion Phillips; Daniel Dubé; Pieter H Bos; Andrew J Clark; Maxwell Gough; Mark L Greenlee; Yimin Jiang; Keith Jones; Masato Kitamura; John Leonard; Tongzhu Liu; Philip J Parsons; Aranapakam M Venkatesan
Journal:  Org Lett       Date:  2017-09-06       Impact factor: 6.005

Review 3.  The Mukaiyama aldol reaction: 40 years of continuous development.

Authors:  Jun-ichi Matsuo; Masahiro Murakami
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-23       Impact factor: 15.336

4.  Total synthesis of (+)-alpha-onocerin in four steps via four-component coupling and tetracyclization steps.

Authors:  Yuan Mi; Jürg V Schreiber; E J Corey
Journal:  J Am Chem Soc       Date:  2002-09-25       Impact factor: 15.419

5.  Scalable Total Syntheses and Structure-Activity Relationships of Haouamine A, B, and their Derivatives as Stable Formate Salts.

Authors:  Hirokazu Tsukamoto; Saki Nakamura; Akito Tomida; Doi Takayuki
Journal:  Chemistry       Date:  2020-04-14       Impact factor: 5.236

6.  Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis.

Authors:  Fenghai Guo; Michael D Clift; Regan J Thomson
Journal:  European J Org Chem       Date:  2012-07-16

7.  Oxidation of silyl enol ethers by using IBX and IBX.N-oxide complexes: a mild and selective reaction for the synthesis of enones.

Authors:  K C Nicolaou; David L F Gray; Tamsyn Montagnon; Scott T Harrison
Journal:  Angew Chem Int Ed Engl       Date:  2002-03-15       Impact factor: 15.336

8.  Concise synthesis of the bicyclic scaffold of N-methylwelwitindolinone C isothiocyanate via an indolyne cyclization.

Authors:  Xia Tian; Alexander D Huters; Colin J Douglas; Neil K Garg
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005
  8 in total

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