Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides

Stephen W. Laws; Lucas C. Moore; Michael J. Di Maso; Q. Nhu N. Nguyen; Dean J. Tantillo; Jared T. Shaw

doi:10.1021/acs.orglett.7b00468

Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides

Stephen W. Laws, Lucas C. Moore, Michael J. Di Maso, Q. Nhu N. Nguyen, Dean J. Tantillo, Jared T. Shaw

Chemistry

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

A diastereoselective base-catalyzed Mannich reaction of cyclic, enolizable anhydrides and N-sulfonyl imines for the synthesis of δ-lactams is reported. This anhydride Mannich reaction tolerates imines derived from aryl and enolizable aldehydes. A base-catalyzed product epimerization pathway ensures high anti diastereoselectivity in aryl and achiral enolizable imines.

Original language	English (US)
Pages (from-to)	2466-2469
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.7b00468
State	Published - May 19 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A diastereoselective base-catalyzed Mannich reaction of cyclic, enolizable anhydrides and N-sulfonyl imines for the synthesis of δ-lactams is reported. This anhydride Mannich reaction tolerates imines derived from aryl and enolizable aldehydes. A base-catalyzed product epimerization pathway ensures high anti diastereoselectivity in aryl and achiral enolizable imines.",

author = "Laws, {Stephen W.} and Moore, {Lucas C.} and {Di Maso}, {Michael J.} and Nguyen, {Q. Nhu N.} and Tantillo, {Dean J.} and Shaw, {Jared T.}",

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doi = "10.1021/acs.orglett.7b00468",

language = "English (US)",

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T1 - Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides

AU - Laws, Stephen W.

AU - Moore, Lucas C.

AU - Di Maso, Michael J.

AU - Nguyen, Q. Nhu N.

AU - Tantillo, Dean J.

AU - Shaw, Jared T.

PY - 2017/5/19

Y1 - 2017/5/19

N2 - A diastereoselective base-catalyzed Mannich reaction of cyclic, enolizable anhydrides and N-sulfonyl imines for the synthesis of δ-lactams is reported. This anhydride Mannich reaction tolerates imines derived from aryl and enolizable aldehydes. A base-catalyzed product epimerization pathway ensures high anti diastereoselectivity in aryl and achiral enolizable imines.

AB - A diastereoselective base-catalyzed Mannich reaction of cyclic, enolizable anhydrides and N-sulfonyl imines for the synthesis of δ-lactams is reported. This anhydride Mannich reaction tolerates imines derived from aryl and enolizable aldehydes. A base-catalyzed product epimerization pathway ensures high anti diastereoselectivity in aryl and achiral enolizable imines.

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U2 - 10.1021/acs.orglett.7b00468

DO - 10.1021/acs.orglett.7b00468

M3 - Article

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SP - 2466

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -

Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides

Abstract

ASJC Scopus subject areas

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