Asymmetric induction in an enammonium-iminium rearrangement. Mechanistic insight via NMR, deuterium labeling, and reaction rate studies. Application to the stereoselective synthesis of pyrroloisoquinoline antidepressants

Kirk L. Sorgi; Cynthia A. Maryanoff; David F. McComsey; David W. Graden; Bruce E. Maryanoff

doi:10.1021/ja00165a048

Asymmetric induction in an enammonium-iminium rearrangement. Mechanistic insight via NMR, deuterium labeling, and reaction rate studies. Application to the stereoselective synthesis of pyrroloisoquinoline antidepressants

Journal of the American Chemical Society ◽

10.1021/ja00165a048 ◽

1990 ◽

Vol 112 (9) ◽

pp. 3567-3579 ◽

Cited By ~ 52

Author(s):

Kirk L. Sorgi ◽

Cynthia A. Maryanoff ◽

David F. McComsey ◽

David W. Graden ◽

Bruce E. Maryanoff

Keyword(s):

Reaction Rate ◽

Stereoselective Synthesis ◽

Asymmetric Induction ◽

Deuterium Labeling ◽

Mechanistic Insight

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Asymmetric induction in an enammonium-iminium rearrangement. Mechanistic insight via NMR, deuterium labeling, and reaction rate studies. Application to the stereoselective synthesis of pyrroloisoquinoline antidepressants [Erratum to document cited in CA112(21):197319w]

Journal of the American Chemical Society ◽

10.1021/ja00178a084 ◽

1990 ◽

Vol 112 (22) ◽

pp. 8217-8217

Author(s):

Kirk L. Sorgi ◽

Cynthia A. Maryanoff ◽

David F. McComsey ◽

David W. Graden ◽

Bruce E. Maryanoff

Keyword(s):

Reaction Rate ◽

Stereoselective Synthesis ◽

Asymmetric Induction ◽

Deuterium Labeling ◽

Mechanistic Insight

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ChemInform Abstract: Asymmetric Induction in an Enammonium-Iminium Rearrangement. Mechanistic Insight via NMR, Deuterium Labeling, and Reaction Rate Studies. Application to the Stereoselective Synthesis of Pyrroloisoquinoline Antidepressants.

ChemInform ◽

10.1002/chin.199034075 ◽

1990 ◽

Vol 21 (34) ◽

Author(s):

K. L. SORGI ◽

C. A. MARYANOFF ◽

D. F. MCCOMSEY ◽

D. W. GRADEN ◽

B. E. MARYANOFF

Keyword(s):

Reaction Rate ◽

Stereoselective Synthesis ◽

Asymmetric Induction ◽

Deuterium Labeling ◽

Mechanistic Insight

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Asymmetric Induction in the [2,3] Wittig Rearrangement The Stereoselective Synthesis of Unsaturated Alcohols with Three Contiguous Stereogenic Centers

Chemische Berichte ◽

10.1002/cber.19891220130 ◽

1989 ◽

Vol 122 (1) ◽

pp. 193-198 ◽

Cited By ~ 19

Author(s):

Reinhard Brückner

Keyword(s):

Stereoselective Synthesis ◽

Asymmetric Induction ◽

Wittig Rearrangement ◽

Unsaturated Alcohols ◽

Stereogenic Centers

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Stereoselective Synthesis of Skipped Polyols by Substrate-Directed Asymmetric Induction

Organic Letters ◽

10.1021/ol0056325 ◽

2000 ◽

Vol 2 (9) ◽

pp. 1209-1212 ◽

Cited By ~ 11

Author(s):

Thomas Trieselmann ◽

Reinhard W. Hoffmann

Keyword(s):

Stereoselective Synthesis ◽

Asymmetric Induction

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ChemInform Abstract: Stereoselective Synthesis of Alcohols. Part 43. Asymmetric Induction on the Intramolecular Allylboration Reaction of (8-Oxo-2-octenyl) boronates.

ChemInform ◽

10.1002/chin.199407076 ◽

2010 ◽

Vol 25 (7) ◽

pp. no-no

Author(s):

R. W. HOFFMANN ◽

T. SANDER

Keyword(s):

Stereoselective Synthesis ◽

Asymmetric Induction

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ChemInform Abstract: Stereoselective Synthesis of cis- and trans-2,6-Disubstituted 5,6- Dihydro-2H-pyrans Based on 1,5-Asymmetric Induction in Reactions Between Allylstannanes and Aldehydes Promoted by Tin(IV) Chloride.

ChemInform ◽

10.1002/chin.199605047 ◽

2010 ◽

Vol 27 (5) ◽

pp. no-no

Author(s):

R. J. MAGUIRE ◽

E. J. THOMAS

Keyword(s):

Stereoselective Synthesis ◽

Asymmetric Induction ◽

Cis And Trans

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The Sulfinyl Moiety as an Internal Nucleophile. 2. Stereoselective Synthesis of (−)-Galantinic Acid via 1,3-Asymmetric Induction†

The Journal of Organic Chemistry ◽

10.1021/jo026892y ◽

2003 ◽

Vol 68 (14) ◽

pp. 5754-5757 ◽

Cited By ~ 24

Author(s):

Sadagopan Raghavan ◽

S. Ramakrishna Reddy

Keyword(s):

Stereoselective Synthesis ◽

Asymmetric Induction

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Stereoselective synthesis of alcohols, XIX. The sense of asymmetric induction on addition to α-chiral aldehydes

Chemische Berichte ◽

10.1002/cber.19851181010 ◽

1985 ◽

Vol 118 (10) ◽

pp. 3966-3979 ◽

Cited By ~ 57

Author(s):

Reinhard W. Hoffmann ◽

Ulrich Weidmann

Keyword(s):

Stereoselective Synthesis ◽

Asymmetric Induction

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ChemInform Abstract: 1,2-ASYMMETRIC INDUCTION WHEN GRIGNARD REAGENTS ARE ADDED TO ALPHA-AMINOKETONES PART 2, STRUCTURAL EFFECTS, APPLICATION TO THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINOALCOHOLS

Chemischer Informationsdienst ◽

10.1002/chin.197518241 ◽

1975 ◽

Vol 6 (18) ◽

pp. no-no

Author(s):

A. GASET ◽

P. AUDOYE ◽

A. LATTES

Keyword(s):

Stereoselective Synthesis ◽

Asymmetric Induction ◽

Grignard Reagents ◽

Structural Effects

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ChemInform Abstract: Stereoselective Synthesis of Alcohols. Part 19. The Sense of Asymmetric Induction on Addition to α-Chiral Aldehydes.

Chemischer Informationsdienst ◽

10.1002/chin.198603074 ◽

1986 ◽

Vol 17 (3) ◽

Author(s):

R. W. HOFFMANN ◽

U. WEIDMANN

Keyword(s):

Stereoselective Synthesis ◽

Asymmetric Induction

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